Vacation Rentals By Owner In Gloucester, MA

5 Acres | Close to Beaches & Trails | Pet Friendly (w/ Fee) | Apartment + Airstreambrbr'Glamping' with a modern twist, this unique 2-bedroom, 2-bath vacation rental is a destination in and of itself. Spread out amongst dual accommodations, and meet in the middle to gather 'round the fireplace and gaze upon coastal views. But don't forget to venture out and explore — between the beaches of Gloucester and the witch houses of Salem, there's no shortage of sights to see and adventures to have!brbr-- THE PROPERTY --brbrC0456321070brbrSLEEPING ARRANGEMENTSbr- Bedroom 1 (House): 1 queen bedbr- Bedroom 2 (House): 1 twin bunk bedbr- Airstream: 1 full bed, 1 twin bedbr- Additional Sleeping: 1 portable cribbrbrHOME DETAILSbr- Smart TV, books, board gamesbr- Dining table, gas fireplacebr- 1 full bath w/ shower & soaking tubbr- Newly renovated, modern furnishings & decorbrbrHOME KITCHENbr- Induction cooktop & microwave ovenbr- State-of-the-art appliances, freezer drawerbr- Cooking basics, dishware/flatwarebr- Keurig coffee makers, tea kettle, toasterbrbrAIRSTREAM FEATURESbr- Dining booth, Smart TV, Keurig coffee makerbr- Kitchen w/ microwave, mini fridge & stovetopbr- 1 full bath w/ standing showerbrbrOUTDOOR AMENITIESbr- Patio w/ dining set & solo stove fire pitbr- 5-acre yard w/ trails & birdwatchingbr- Bistro-lit courtyard w/ seating & diningbr- Wood-burning fireplace, outdoor heatersbr- Chaises, gas & charcoal grillsbr- Outdoor shower & speakersbr- Hammock, kayak, hilltop Essex bay viewbrbrGENERALbr- Free WiFi, washer/dryerbr- Linens/towels, complimentary toiletriesbr- Hair dryer, iron/board, clothing steamerbr- Beach chairs, towels & umbrellabr- Mini-split heating & air conditioningbrbrFAQbr- Pet fee (paid pre-trip)br- Homeowner on-site (main house, top floor)brbrACCESSIBILITYbr- Single-story home, 1-2 steps requiredbrbrPARKINGbr- Garage (1 vehicle)br- Driveway (2 vehicles)brbr-- THE LOCATION --brbr- 3 miles to Wingaersheek Beachbr- 5 miles to Gloucester attractions - Stage Fort Park, Gloucester HarborWalk, Ten Pound Island Lighthouse, Hammond Castle Museum, Cape Ann Museum, fishing charters, whale watching toursbr- 7 miles to Good Harbor Beachbr- 10 miles to Halibut Point State Parkbr- 16 miles to Downtown Salembr- 33 miles to Boston Logan International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome--because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $50 fee (+ fees & taxes)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- The single-story main house requires 1 small step up for entry, while the Airstream requires 2 steps for accessbr- The homeowner lives on-site in the top floor of the main house and may be present during your stay

Airstream & Ocean View: Unique Gloucester Getaway

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$1072.29

Welcome to a completely reimagined coastal retreat in the heart of Annisquam, where timeless New England charm meets modern luxury. Just a short 2-minute walk to private neighborhood beaches, this newly renovated home is designed for families and groups looking to relax, gather, and experience the best of Cape Ann.brbrNEW PHOTOS POSTING MEMORIAL DAY WEEKEND!brbrTHE SPACE: This home has been fully renovated from top to bottom, offering a rare combination of high-end finishes, spacious layout, and true multi-family comfort.brbrWith over 2,400 square feet of thoughtfully designed living and sleeping space, the home comfortably accommodates up to 10 guests without compromise.brbrSleeping Arrangements:br3 spacious bedrooms. 2 full suites with King Beds and private bathrooms. And one comfortable bedroom with Queen Bed. Additional, 3rd level large room with king AND 2 twin beds — perfect for kids or additional guestsbrbrBathrooms:br3 full bathrooms + 1 half bathbr(No waiting lines, even with a full house!)brbrDESIGNED FOR GATHERINGbrbrThe home features a large, open-concept living space and kitchen, ideal for entertaining, cooking, and spending time together.brbrBrand new chef’s kitchen with modern appliancesbrMultiple indoor living areas with 3 separate TVs — perfect for families sharing spacebrBright, airy interiors with natural light throughoutbrWhether you're hosting dinner, watching the game, or giving kids their own space — this layout works.brbrOUTDOOR LIVINGbrbrStep outside to enjoy a 2 large private decks and outdoor entertaining area, complete with:brDining space for group mealsbrBBQ grillbrComfortable seating for relaxing after the beachbrOUTDOOR SHOWER!brbrLOCATION: ANNISQUAM (PRIVATE GEM OF CAPE ANN)brbrLocated in the quiet, highly sought-after village of Annisquam, this home offers:brbr2-minute walk to private beachesbrPeaceful, residential setting (no crowds)brClose proximity to Gloucester and RockportbrEasy access to restaurants, boating, and coastal activitiesbrbrAnnisquam is known for:brbrCalm waters (great for kids)brScenic coastal viewsbrClassic New England charmbrbrThis home is ideal for:brbrMulti-family vacationsbrExtended family gatheringsbrCouples traveling togetherbrSummer-long staysbrbrThe combination of king bedrooms + multiple bathrooms + flexible sleeping space is extremely rare in this area.brbrWHAT MAKES THIS HOME DIFFERENTbrbrBrand new, high-end renovationbr3 true king bedrooms (not common locally)brWalk to private beach (no driving required)brMultiple living zones (no crowding)brDesigned specifically for group comfortbrbrBOOKING NOTESbrbrPeak summer rentals are typically Saturday–SaturdaybrWeekly rentals preferred in July and AugustbrEarly booking recommended — Annisquam inventory is limited

BRAND NEW, Complete renovation: 4-Bedroom, 3.5 Bath, private Annisquam Gem!

Gloucester, Massachusetts, United States

Bed

Bath

12

Sleeps

$1489.8

La Casa De La PlayabrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to your enchanting getaway in Gloucester, MA, where oceanfront luxury meets serene privacy. This inviting abode is just a stone's throw away from the exclusive Wingaersheek Beach, also known as the revered “Coffin’s Beach.” Nestled on two lots, this home offers a tranquil retreat that is perfect for families and friends looking to escape the hustle and bustle of everyday life. With breathtaking views and direct beach access, this vacation rental is a dream come true that you'll want to return to year after year.brbrStep inside to discover light-filled living spaces, particularly the living room, which boasts panoramic vistas of the majestic ocean. Imagine starting your day with a peaceful walk along the powdery white sand dunes or sipping your morning coffee while listening to the gentle waves lapping at the shore. The home is designed for comfort and relaxation, featuring a wood-burning fireplace, partial AC, and a fully equipped kitchen that makes meal preparation a breeze.brbrThe property is perfect for families, with a shallow tide that is safe for kids and a 1.5-mile crescent-shaped beach ideal for lounging, walking, or running. After a day of beachcombing or whale watching, retreat to your cozy haven and fall asleep to the soothing sounds of the ocean waves. brbrLocated just a short drive from downtown Gloucester, you'll have easy access to fantastic restaurants, shops, and cultural attractions. Explore nearby towns like Manchester By The Sea and Essex, known for their charming antique stores and delicious lobster shacks. Whether you're seeking adventure or relaxation, this Gloucester home is the perfect base for your coastal getaway. Book your stay today and experience the magic of this captivating oasis!brbrThings to KnowbrbrYou must go through dune grass to get down to the private beach. It is not a well manicured path, as the dune grass is in place to keep erosion at bay.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 4 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Private beachfront escape on Coffins Beach w/ amazing views & private beach

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$870.66

Enjoy your own private BEACH on this waterfront property with easy access to the Annisquam River and the Atlantic Ocean. Newly constructed luxury waterfront townhouse vacation rental with 2,500 sq ft of living space and modern amenities that includes 3 bedrooms including a Primary Suite and 3 bathrooms with a (2) car garage on a private setting that can comfortably sleep 6 people. We offer 3 & 5 night rentals, as well as, weekly and monthly rentals throughout the year for spring, summer, fall and winter seasons see calendar for availability ! brbrWith just 5 steps to the water you can receive all the perks of this property that include swimming, bathing, kayaking, SUP, fishing or boating at your leisure. There is a lawn overlooking the private BEACH area with a paver patio and a gas grille ready for a barbecue or cookouts. Located on the mouth of the Annisquam River with easy access to Gloucester Harbor, Wingaersheek Beach and the Atlantic Ocean. Enjoy swimming, kayaking, SUP, boating and bathing from your own beachfront. Want to get to the downtown and enjoy the restaurants, main street shopping, whale watching tours, golfing or the local festivals you are less than 3 miles away by taking a left at the end of Stanwood Avenue on to Route 133 (Essex Avenue).brbrThis New England Craftsman Custom Home has high quality finishes throughout and beautiful water views from the almost anywhere on the first floor and throughout the Primary Suite. The first floor includes custom built Kitchen Cabinets, Thermador appliances, Butler Pantry and a custom built Bar with an open floor plan that includes a large Dining Room and Family Room. Plenty of seating at the 84 Kitchen Island that includes Quartz - wrapped countertops. The second floor includes (3) bedrooms, Loft Area, Laundry Room and Common Bath. Primary Suite includes a Sitting Room, Primary Bath with custom shower and stand alone tub with his / her walk in closets. Common Bath has subway tile shower / tub with wall tile and his / her vanities. Design lighting fixtures, white oak hardwood floors, James Hardie cedar shake siding, cobblestone driveway, 10' x 10' paver patio, professional landscaping, Kohler plumbing fixtures, Emtek hardware and a Kohler Home Generator just in case power is lost are just some of the finishing touches included in this home.brbrThe Stanwood Point Landing Boat Ramp ramp is walking distance from the property just down the street off Stanwood Avenue. There are (2) additional off street parking spaces across the street for your guests, as well as parking in the garage and cobblestone driveway.brbrNo smoking. No pets. No events or parties. Linens and beach - bath towels included.brbrAll NEW quality furniture throughout that includes the following:brbrFamily Room: includes leather couch and loveseat in Family Room with oak / white cocktail table and Smart TV hanging over the fireplace. brbrDining Room: includes a 86 Black Sand Dining Room Table with White Sand Chairs and (3) Counter Stools at the Kitchen Island.brbrPrimary Bedroom: includes a King Bed (white) with (2) end tables and matching dresser with couch and coffee table in the Sitting Room along with Media Center and Smart TV.brbrLoft Area: includes a sofa chair and end table with a desk with chair for an iPad or Laptop computer.brbrBedroom # 1: includes (2) Queen Beds (Blueberry) with white night table in between them and large walk in closet.brbrBedroom # 2: includes (1) King Bed (white) with matching Drawer Chest and (2) end tables.brbrOutdoor furniture: includes (6) Folding Lounge Chairs, (2) Adirondack Chairs, Dining Patio set with (6) chairs and a Charbroil direct gas hookup barbecue grille (no propane tanks needed). Outdoor security cameras.

Private Beach New Luxury Waterfront Vacation Rental Annisquam River

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$429.32

Longview HousebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrVisit the charming coastal town of Gloucester, MA, and choose this beautiful home as the perfect retreat for your next vacation. Conveniently located just an 8-minute walk from the Commuter Rail, shops, restaurants, downtown area, beaches, and the Boulevard, you'll have easy access to all that Gloucester has to offer. Take schooner and lighthouse tours ( to see 5 iconic lighthouses -- one of which they can see from the house) or visit the many beaches in the area (get there early). Beyond the property, Gloucester beckons with a variety of activities for all interests. From beachcombing and whale watching to shopping and dining at local restaurants, there's something for everyone. Explore the nearby towns of Essex and Manchester-By-The-Sea, or take a trip to Salem to discover its fascinating history. Whether you're seeking a relaxing coastal getaway or an action-packed adventure, this house serves as the ideal base for your Gloucester escapades.brbrStep inside this lovely home and enjoy a range of amenities, including ocean views, a jetted tub and central AC. The spacious deck and patio provide the ideal setting for outdoor gatherings, while the gas grill is perfect for summer barbecues. Challenge your friends and family to a game of cornhole or just sit back and breathe in the ocean air. Inside, you'll find a well-equipped kitchen with modern appliances, a washer/dryer for convenience, and comfortable living spaces to relax in after a day of exploring.brbrWith its dog-friendly policy, this house ensures that every member of the family can join in on the fun. Whether you're lounging on the deck with your furry friend by your side or heading out for a day of sailing or paddleboarding, you'll create unforgettable memories in this coastal gem. Book your stay now and immerse yourself in the beauty and charm of Gloucester!brbrThings to KnowbrbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 2 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Beautifully renovated home walk to boulevard, town & train

Gloucester, Massachusetts, United States

Bed

Bath

9

Sleeps

$356.26

Haskell Street HideawaybrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrEscape to this tranquil Gloucester gem on your next getaway! Nearby, you'll love having easy access to Bass Rocks Golf and Tennis Club, Good Harbor Beach, Rocky Neck, Gloucester Harbor, and the infamous Back Shore. Delicious, fresh seafood, and just as wonderful shops can all be indulged in - downtown. And to make your days at the beach even better, appreciate the amenities this home offers to guests. These include; a beach cart, four beach chairs, a cooler, and outdoor games.brbrAfter a day full of sun, sand, and surf, spend time on the home's front deck and unwind. Or, rinse off in the outdoor shower. When you're ready to head in, you'll instantly take notice of the spacious main living area. Adorned with ample seating, a large TV, and charming coastal-themed decor, the ambiance of this room is inviting and cozy! Relax by the electric fireplace and curl up with a good book. In the nearby full kitchen, utilize the stainless steel appliances and plentiful meal prep space when you can resist dining out on the town. Homemade meals or takeout can be enjoyed at the dining table, mini breakfast bar, or alfresco. brbrIn each of the bedrooms, you'll love their bright and homey feel. Settle in and make the space your own as the sunlight pours in from the home's many windows. brbrCome nightfall, enjoy more of that balmy Massachusetts air from the comfort of the home's enclosed yard, wraparound deck, or gathered around the firepit. Mix in a barbecued meal, prepared on the private gas grill, and you're sure to craft a memorable night! brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brStreaming services available with guests’ own account(s).brbrParking notes: There is free parking available for 3 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Classic charmer near the coast with with a firepit, outdoor shower, & beach gear

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$1616.33

Magnolia TidesbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrMagnificent sunrise views await at this oceanfront charmer! Modernly updated and full of light, the interior of Magnolia Tides displays an open-concept layout, separate living quarters in the basement, and ocean views throughout. With so much space to sprawl out in, this home is great for multi-generational family stays. Sit back and enjoy each other's company from one of the living room sofas, while never losing sight of the crashing blue waves beyond. When you get hungry, the chef's kitchen boasts gleaming countertops, stainless steel appliances, and all of the nifty gadgets you need to prepare your favorite dishes. brbrFull and content, gather around the dining room table for a board game or try to catch sight of a whale or seal from the telescope. The bedrooms are equally lovely, all adorned with high-quality linens, soothing color palettes, and partial air-conditioning. The interior conveniences extend to a private washer/dryer, internet access, a Ping-Pong table, and beach gear for your days in the sand. brbrOn the spacious deck, fire up the brand-new gas grill and host a quintessential coastal barbecue, followed by a lovely alfresco dining experience under the shade of the electric awning. After your meal, walk along the home's gardens or opt for a peaceful sway in the hammock. brbrWhen you are ready to see the sights of Gloucester, head for Rafes Chasm Park, Stage Fort Park, Cape Ann Whale Watch, the North Shore Music Theatre, and all of the area's delicious restaurants, vibrant boutiques, and stunning beaches. Boston is a quick day trip away as well! brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brStreaming services available with guests’ own account(s).brbrParking notes: There is free parking available for 4 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Modern oceanfront home with scenic deck, grill, games, chef's kitchen, & W/D

Gloucester, Massachusetts, United States

3

Bed

3

Bath

6

Sleeps

$540.38

Little River RetreatbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNestled in a quiet neighborhood of Gloucester, MA,this charming cottage offers breathtaking river views from a private balcony and a peaceful retreat from the hustle and bustle of everyday life. With deeded river access just two houses away, it is perfect for launching kayaks or enjoying a leisurely day on the water. A neighborhood boat ramp nearby provides easy access for smaller boats, providing endless opportunities for adventure right at their doorstep.brbrThe cottage features a spacious deck and patio, complete with comfortable outdoor furniture and a gas grill, making it an ideal spot for al fresco dining or evening gatherings around the firepit. Inside, you'll find a well-equipped kitchen with modern appliances, including a fridge, stove, and dishwasher, ensuring you have everything you need for a delightful stay. The cozy living area is perfect for relaxing after a day of exploring, with cable TV and partial AC for your comfort.brbrConveniently located within walking distance to the train station and easily accessible to the highway, this cottage is just a short drive from the stunning beaches of Wingaershaek and Good Harbor, as well as downtown Gloucester. Whether you're looking to spend your days beachcombing, kayaking, or simply soaking in the picturesque surroundings, this property is the perfect home base for your Gloucester getaway. Book your stay today and experience the beauty and tranquility of this riverside retreat!brbrThings to Knowbrbr-This is a very quiet family neighborhoodbrbrParking notes: There is free parking available for 3 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

River view home w/ deck, river access, near beaches and train

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$108.38

Springtime photos are on the way!! Take it easy at this unique and tranquil getaway in front of Smith Marina. The condo has everything to make yourself at home while enjoying the area. A balcony for sitting out and enjoying the water view. Short walk to ROCKY NECK, a longstanding art colony with many galleries and shops.brbrAn open living and kitchen area with a hand-crafted high-top table that can be used for dining or working. All with a view to the water. Balcony with seating for 2 (extra chairs can be provided). Small bathroom. Bedroom with a full-sized post bed. Closet space and a small bureau. brNeighbors are friendly :)

Apartment

Marina View, Walk to Niles Beach & Rocky Neck

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$571.51

Paula's SuitebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrCentrally located in the charming coastal town of Gloucester, this apartment offers a comfortable and convenient retreat for your vacation getaway. Just steps from your door, you'll find a variety of activities and entertainment to enjoy, from fabulous restaurants and shopping to beachcombing and whale watching. Explore all this vibrant downtown area has to offer or catch a show at the nearby cinemas and theaters. brbrStep inside this cozy apartment and unwind in the spacious living room, or enjoy a meal in the dining area. There is plenty of space to spread out, spend time with your family and friends or just relax. With many amenities, including a washer/dryer, central air-conditioning, WiFi, and a well-equipped kitchen with modern appliances, you'll have everything you need for a relaxing stay. brbrThings to KnowbrbrParking notes: There is free parking available for 1 vehicle.brbrSecurity camera details: camera at front doorbrcamera facing the parking lotbrbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Apartment

Centrally located open concept apartment with parking, central AC, & W/D

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$448.13

Beau's Beach HousebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrAn exceptional stay awaits you and yours at this beautifully updated vacation home in a quiet, highly desirable East Gloucester neighborhood. The home's prime location situates you near many fantastic walking trails, great restaurants, and scenic coastal drives. You'll love being located steps from Rocky Neck, Good Harbor Beach, and Niles Beach, and a short driving distance to downtown, Manchester By the Sea, Rockport, and Essex.brbrUpon entering, you will take notice of the welcoming, open-concept layout complete with hardwood flooring throughout. The comfy living area invites you to spread out with your loved ones and rest after an exciting day exploring your surroundings. Stream your favorite movies and shows on the Roku smart TV, and when you get hungry, utilize the well-equipped kitchen to prepare mouthwatering culinary masterpieces for your group. In the kitchen, you will find all the essential appliances, including a Keurig coffee maker. brbrUpstairs, you'll find the equally comfortable bedrooms. Additional perks include a desk on the first floor, board games, and a washer/dryer on the second floor. For great comfort, there is an air-conditioner/heat unit on the main floor, as well as in each of the bedrooms.brbrThings to KnowbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrAll guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AMbrNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 4 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Coastal retreat steps to the beach with smart TVs, desk, grill, children's items

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$400.63

- This cozy antique cottage with historic charm is in a quiet tucked away neighborhood of Gloucester - the perfect spot for a retreatbr- One of a kind SAUNA and fire pit in the backyardbr- Hi-speed WiFibr- Plenty of off street parking spotsbr- Fully equipped + stocked country kitchen with unique characteristics like an antique stovebr- A 10 minute drive to all the attractions of Downtown Gloucesterbr- Walk to nearby hiking trails, beautiful Lighthouse Beach and the quaint village of Annisquambrbr→ Warm and light filled sunroom with dining table to enjoy peaceful mealsbr→ Roku TV equipped to stream all your favorites br→ 3 season sunroom porch with daybed closes off for an additional private sleeping spacebr→ Living room with a pull out sofa also closes off for a third private sleeping spacebr→ Plenty of off-street parkingbr→ Fully equipped + stocked kitchenbr→ Outdoor shower and grill perfect for warmer days spent in the yard br→ Newly fenced in yard, perfect for your furry friends!brbrPLEASE NOTEbr- The stairs are steep to the second floor so we don’t advise for anyone with mobility issues. There is a daybed and pull out sofa on the first floor. br- The 3 season porch is not heated so it should only be used in warmer months! The sunroom is also 3 season but we provide a space heater for cooler months. brbr*Rental Agreement is required to be signed after reservation has been confirmed. Failure to comply will result in the cancellation of reservation.br*Damage Protection included - we have included a $28 charge in your total quote that covers your purchase of $1500 of all risk damage protection coverage on the rental property. This protection is purchased in lieu of a cash damage deposit. Coverage details are spelled out in the rental agreement. brbr

Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$472.53

Nestled in a serene, private, and quiet dead-end street, this delightful space in Gloucester Massachusetts, offers a perfect blend of comfort and convenience. Just a 10-minute walk to downtown, and a mere 15 minutes to Stag Fort Park. The location is ideal for exploring the best of what Gloucester has to offer. Upon entering, you will find yourself in a cozy living room that that doubles as a bedroom, equipped with a comfortable queen size bed and a smart TV and Wi-Fi. The space is thoughtfully designed to maximize comfort and functionality. The renovated bathroom boasts an awesome Bio Bidet toilet seat and Bluetooth speaker/lights adding a touch of luxury to your stay. The fully equipped kitchen includes a gas stove, dishwasher, washer & dryers, and all the necessary cooking utensils. Preparing your favorite meals here is a breeze. One of the highlights is the balcony/deck, a perfect spot to enjoy your morning coffee or relax amidst the charming views. About a 3-block view to the Annisquam river-Mile Marker/Cape Ann Marina across the way. Smoking is allowed on the balcony, and the property is 420 Friendly, catering to all your relaxation needs. Being on the first floor, the space provides easy accessibility, making it convenient for all guests. 1 Parking space is provided across from the front door.

Hilltop Hideaway LARGE 2 room studio with amazing sunset views, deck and kitchen

Gloucester, Massachusetts, United States

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Bath

Sleeps

$371.0

Unique Tudor Carriage House, beamed through out with 2 1/2 story Great Room with french doors overlooking grand lawn. Walk to the sandy beach and seasonal sunset views. Minutes from downtown historic Gloucester, with its famous fisherman's statue, many shops, restaurants and museums, close to artsy Rockport and 45 minutes to Boston. Bring your bike or your SUP.

English Tudor Manor-Walk To Beach

Gloucester, Massachusetts, United States

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Bath

Sleeps

$270.29

Bianca's HousebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNestled in the heart of Gloucester, Bianca's House offers a pleasant city getaway for you and your loved ones! Entertainment is never out of reach as numerous restaurants, parks, beaches, musical theatres, and local boutiques are located mere minutes away. brbrWhen spending a night in, settle down and enjoy your favorite TV shows and movies on the living room's comfortable seating. Playful competition is sure to arise over board games - played at the dining table. When hunger arises, the well-equipped kitchen boasts all of the necessities needed to whip up delicious dishes. A good night's rest will come effortlessly in both of the bedrooms, adorned with high-quality linens and central air-conditioning. brbrBefore you head to bed, sip and reminisce on the patio's dining set - cheering to another vacation well-booked! brbrThings to KnowbrPlease note that this retreat is located next to the commuter train and you will be able to hear the bells and whistles from inside the home as it goes by.brbrParking notes: Street parking is available on a first-come-first-serve basis; parking is not guaranteed.brbrbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Centrally located charmer with expansive patio, board games, & central AC

Gloucester, Massachusetts, United States

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Sleeps

$554.32

Mill Pond Cottage offers a unique blend of old-world charm and modern comfort. With three bedrooms and a stunning view of the pond, it’s the perfect destination for your relaxing getaway.brbrBuilt in the late 1800s, Mill Pond Cottage exudes a timeless elegance that transports you back to a bygone era. The moment you step inside, you’ll be captivated by its rich history and architectural details. From the hardwood floors to the crown molding, every corner is infused with character.brbrDespite its historic nature, this house has been thoughtfully renovated to provide all the conveniences of modern living. Air conditioning splits ensure that you stay cool during warm summer days, while still preserving the integrity of the original design. You can truly have the best of both worlds – stepping into a piece of history without compromising on comfort.brbrWith three bedrooms, there’s ample space for families or groups of friends to unwind after a day exploring Gloucester’s charming streets or nearby beaches. Each bedroom has been lovingly decorated with a mix of antique furnishings and contemporary touches, creating a cozy atmosphere where you can retreat and recharge.brbrLocated just minutes away from Gloucester’s vibrant downtown area, this vacation rental provides easy access to local attractions, shops, and restaurants. Whether you’re seeking outdoor adventures along Cape Ann’s scenic coastline or immersing yourself in Gloucester’s rich maritime history, there’s something for everyone here.brbrNo pets. No smoking. No events or parties.

Mill Pond Cottage: Timeless Gloucester Elegance

Gloucester, Massachusetts, United States

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Sleeps

$637.17

Spectacular, furnished 2-bedroom apartment is just moments from the North Shore's iconic Good Harbor Beach, Bass Rocks Golf Club, colorful Rocky Neck & historic Gloucester with its storied seaport & burgeoning cultural & dining scene. This beautifully renovated oceanfront apartment rental makes the most of its spectacular setting in a 2-unit Victorian home with 2 bedrooms (1 King & 1 Queen), 1 1/2 bathrooms, fireplaced living room w/ Queen sofa bed, quartz kitchen countertops & laundry in unit.brbrThis beautifully updated grand Victorian property oozes character and beachy charm while offering a prime oceanfront location in the heart of the Back Shore. Moments from all the reasons to live on the North Shore's most compelling coastline - a short walk to Good Harbor Beach or explore the rock beach right outside; this private apartment offers all the comforts of a “home away from home.” br

Apartment

Gorgeous Oceanfront 2-Bdrm Apartment w/ Fireplace

Gloucester, Massachusetts, United States