Home Vacation Rentals By Owner In Essex, MA

Showing 12 Of 12 Vacation Rentals
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Exceptional(30)

$601.66

/ Nightly
Cottage

Spacious Lakefront Escape w/ 3 Baths + Bonus Bed

Essex, Massachusetts, United States

brRelaxing 2 bedroom/3 bath + an extra bed in room off of living room - sleeps 6. The house sits on a lakefront property with a large backyard, grill, 2 new patios, and a private dock with canoe, kayak, lake floaties, life jackets, fishing poles, hammock, and kids climbing structure. brbrWe are including pictures of the downstairs as this has remained the same. Some furniture will be updated but the long dining table, chairs, work desk and couch remain the same. The second floor of the house was fully renovated in 2024/25. We are still completing the master bath. We will be posting updated pictures of the upstairs shortly but if you would like more details, please message me. brbrThis place truly is a little slice of heaven. As soon as you walk into the living room you are met by a breathtaking view of the lake and behind you sits an incredible fireplace. The fireplace works; we ask that only duraflame logs are used. The kitchen is fully equipped with plates and dishes for up to 6 people. Work from home desk in the sunroom overlooking the lake with a sit down / standup desk option. There is one bed on the the first floor in its own room off of the living room. This room does not have doors so it is not fully private but it is a step up from a pullout couch as you do not need to convert the living room into a bedroom. This downstairs room has a full size bed. There is a full bathroom on the first floor with toilet and shower.brbrUpstairs on the second floor are two new bedrooms, both with king size beds. The master bedroom has three large windows that overlook the lake. There are also two new bathrooms, one with a shower over a soaker tub and the other with a beautiful stand alone soaker tub and a large separate shower.brbrThe house has driveway parking for up to 3 cars. Lots of walking trails that can be reached from the house. Downtown Essex is only a short bike ride or 5 minute car ride away.brbrFor anyone with children, we offer a pack n play upon request. We also have a high chair, safety gate, a set of toddler dishes, an indoor play tent, balance bike, and lots of toys. We have an extra child size blow up mattress upon request.brbrFor anyone looking to work from the house we have an Uplift work from home desk located in the sunroom overlooking the lake.brbrWe have a yoga mat, light weights, and exercise bands for anyone that enjoys a workout at home. Yoga overlooking the lake is truly wonderful!brbrThe lake is a wonderful place to visit any time of year. Lots of charming towns to visit nearby. Swimming and boating in the summer, ice skating and ice fishing in the winter. Boston is a 45 minute drive or an hour by train. The train station is 15 minutes from the house in Manchester-by-the-sea. There are several beaches close by, including the famous singing beach in Manchester. The house is a 5 minute drive from the local restaurants and brewery in Essex, including The James which is family run and looks forward to hosting our guests! Several grocery stores 15-20 minutes away.
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Bath 3

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Sleep 6

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Exceptional(27)

$679.14

/ Nightly
Private Vacation Home

❤️ of Cape Ann, - Historic Antique Colonial yet new & modern Close 2 Everything

Essex, Massachusetts, United States

Large beautifully restored and renovated 1888 colonial home with deep historical roots in Essex, in the heart of beautiful Cape Ann. This all 1 level (1st floor) completely renovated space offers 3 bedrooms, (with possible use of a 4th), full bathroom and loaded kitchen, with original hardwood floors and details throughout. You'll be most comfortable and at home and enjoy all that beautiful Cape Ann has to offer, within 15 minutes of Salem) come relax on the large farmers porch which awaits you. Ideally location of all Cape Ann attractions and North Shore, SALEM, and IPSWICH for sure.
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Sleep 8

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Exceptional(30)

$360.79

/ Nightly
Apartment

Relaxing Rivers Edge Main Street Retreat

Essex, Massachusetts, United States

Apartment located in the heart of Essex directly across from the Essex Historical Society and Shipbuilding Museum. Enjoy this private first floor apartment in a owner occupied home with common yard space. Just steps away from many of Essex’s finest restaurants including Woodsman’s where the fried clam was invented. Essex is also known for its great antiquing, don’t forget to stop into Sea Meadow for local gifts and treasures.
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Sleep 6

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Exceptional(10)

$544.54

/ Nightly
Cottage

Coastal Cottage on Private Island, overlooking the Essex Great Marsh

Essex, Massachusetts, United States

Minutes from Cranes Beach, Gloucester, Ipswich and downtown Essex, you will have your own cottage on a 14 acre, three-cottage compound. The architect designed cottages combines spectacular views with modern amenities. Enjoy a swim off the dock, or a drink at the fire pit. Guests can also book a trip with Captain Moore, who runs Lowe Island Fish Camp from the same property.
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Sleep 5

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Exceptional(6)

$1720.18

/ Nightly
Private Vacation Home

Renovated Home with Private Pool

Essex, Massachusetts, United States

Spacious vacation home with lots of activities and spaces to relax. Newly renovated. Something for everyone. Enjoy the private saltwater pool with sun shelf and deep end, hot tub, fire pit, pond, paddle boat, canoe, and paddle boards, pool table, skee ball, and exercise room. Pond ice skating in the winter. Take a nature walk on the hiking trails abutting the property. Close to restaurants, fishing charters, area beaches, whale watches, schooner adventures, diving, movie theater, museums.
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$733.93

/ Nightly
Private Vacation Home

Robbin's Island - Panoramic Waterviews

Essex, Massachusetts, United States

New for 2026! Few places on the North Shore stop you in your tracks quite like this. Perched above the marsh with Essex Bay stretching out before you, this modern two-bedroom, two-bath home delivers the kind of waterfront experience most people only dream about - and it's yours from the moment you arrive.brbrEnter into the open space main room with a glass wall facing the water, a fully equipped kitchen, dining and living area, and a deck that can be left open or screened in, creating the perfect setting for a peaceful coastal escape immersed in the natural beauty of Essex Bay.brbrThe primary bedroom is perfectly positioned to face the water, offering peaceful bay views, while the second bedroom enjoys island-facing water views and its own tranquil outlook. Upstairs, the bright living/TV room opens onto a spacious deck - an ideal place to unwind, enjoy your morning coffee, or take in the sweeping scenery.brbrNo smoking. No parties or events.
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Exceptional(3)

$368.61

/ Nightly
Private Vacation Home

NEW - 2 bed / 2 bath+large Deck in the center of beautiful Essex, MA

Essex, Massachusetts, United States

This is a newly listed rental, with first availability in July. Hence we have not had anyone have the opportunity to provide a review yet. Our manager has another property in town with lots of reviews. This property will be managed the same so you can check out her profile and get an idea of service. We put lots of care into our home and the comfort of our guests.brbrCharming 2 bedroom and 2 bath with a third single bed in room off of master - sleeps 5. Large back deck with table and chairs and walking distance to restaurants and shops.brbrWhen you walk in you have an open floor kitchen onto living/eating area with television. There is a half bath off of kitchen. Upstairs there are two bedrooms with queen size beds and both with closets, the master is a walk in closet. Off of the master bedroom is another small room with a single bed. There is also a full bathroom upstairs with bathtub, shower, washer, and dryer.brbrFor anyone with children, we offer a high chair, safety gate, a set of toddler dishes, and some books and toys.brbrWe allow pets with deposit. We ask that they stay off the beds.brbrThere is also a large back deck with eating area, grill, and a shared backyard. The location is very convenient as it is walkable to downtown Essex - restaurants, coffee spots, shipping building museum, ice cream shop, and small gift stores.brbrWe are making some updates including a freshly painted deck, new furniture, new linens and decor. Additional photos will be coming soon!brbrThere are a lot of wonderful activities in walking distance or a short drive away - several beaches very close by, lots of walking/hiking trails, kayaking and cruises available in Essex River, lots of antiques stores, a large flea market, the wonderful Appleton Farm is only a 5 minute drive away, and many other fun things to do and places to visit in the area!brbrAfter booking, we provide a detailed welcome guide with lots of recommendations.brbr2 car parking in driveway.brbrBoston is a 45 minute drive or an hour by train. The train station is 15 minutes from the house in Manchester-by-the-sea. brbrAny specific questions, please do not hesitate to message!
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Sleep 5

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Exceptional(4)

$530.58

/ Nightly
Cottage

Modern Cottage, Private Island, Unparalleled beauty

Essex, Massachusetts, United States

Embedded in the 25,000+ acres of Essex's Great Marsh, Lowe Island Coastal Cottages provide comfortable spaces, modern amenities, exceptional privacy and unlimited beauty. While Cape Ann, Gloucester, Essex, Ipswich and Newburyport supply endless entertainment and restaurant options, guests can choose to hire L.I.F.C. owner Justin Moore to for unforgettable New England Coastal Experiences. A second cottage (King + Queen) is can also be rented for larger parties.
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Sleep 4

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Exceptional(4)

$137.62

/ Nightly
Private Vacation Home

The Little House+Walk to Essex Waterfront+BEACH

Essex, Massachusetts, United States

Escape to the serene beauty of Essex, and experience the coziness of this charming tiny house. This thoughtfully designed space offers the perfect blend of comfort and minimalist design for a memorable getaway. Just a stone's throw from the scenic coastline, the Little House provides an idyllic retreat for couples or solo travelers seeking a peaceful retreat.brbr10 Min Drive to Picturesque Crane Beachbr30 Min Drive to SalembrbrExperience Historic Essex at The Little House & Learn More Below!brbrKEY FEATURES:br☀ Comfortable memory foam queen bedbr☀ Newly Renovated Bathroombr☀ Full kitchen with seating on lower levelbr☀ Hi-Speed WiFi and Roku Smart TV br☀ Exterior Camera present br☀ Walk to Essex Main Street - full of antique shops, seafood restaraunts, and beautiful marsh viewsbrbr☆☆ MAIN LEVEL ☆☆brbrTake advantage of your reserved driveway parking and conveniently pull right up to the historic Little House. Step inside this lovingly restored space and you'll be immediately charmed by all the warmth and light. Original pine floors, high vaulting ceilings, skylights and plenty of windows make this a space you won't soon want to leave! This bedroom and living area offers plenty of space to unpack and unwind after a day of exploring all the North Shore has to offer. brbr☆☆ BATHROOM ☆☆brbrThe bathroom is fully renovated with a walk in tiled shower. Worry about nothing as this thoughtfully stocked bathroom provides all that you'll need to be comfortable during your stay.brbr☆☆ KITCHEN☆☆brbrThe downstairs kitchen is fully equipped with all the appliances, utensils and cookware you need to feel at home. Choose to walk over to Essex's delicious dining options or dine in here at the kitchen table for 2! brbrbr★☆ Book Today & Let Us Take Care Of You at the Essex Little House! ☆★
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Sleep 2

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Exceptional(2)

$560.37

/ Nightly
Private Vacation Home

Winter deal! Charming 3-bedroom house on one floor in Essex

Essex, Massachusetts, United States

Nestled in Essex, this delightful house offers 3 bedrooms - 2 with queen beds and 1 with a bunk bed. With amenities like a hair dryer, heating, Dw, WD, iron, and AC, guests will have an enjoyable stay. The 2 bathrooms provide convenience for all. Experience what Essex has to offer with a stay at our clean and simple house.
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Sleep 6

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Exceptional(8)

$599.46

/ Nightly
Private Vacation Home

Winter deal! Delightful 3-4 bed one floor, 3 baths, fireplace

Essex, Massachusetts, United States

Nestled in Essex, this delightful house boasts 4 bedrooms - 3 with queen beds and 1 with a bunk bed. With 3 bathrooms featuring a bathtub, shower, and jetted bathtub, guests can relax in style. The property also offers heating, AC, DW, WD and an iron for convenience. Enjoy all that Essex has to offer when you stay at our place.
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Sleep 10

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Exceptional(51)

$1200.92

/ Nightly
Country House

Rustic Luxe FarmHouse a Few Miles To Crane Beach: deck &jacuzzi overlooking pond

Essex, Massachusetts, United States

Magical first-period farmhouse circa 1686 near the sea and convenient to all Cape Ann has to offer! Perched among rolling green hills in the Essex countryside, this special retreat features outdoor amenities like an oversized deck with views of the pond that teems with wildlife year round, outdoor screened living room w/ TV, lg sofa, chairs and dining table situated near the glorious herb & flower gardens for your relaxation. Soak in the 8 person outdoor hot tub and taking in the natural beauty the property has to offer!!!brbrIf dates are unavailable please check our SISTER PROPERTY in Rockport MA: https://www.vrbo.com/2589839 adultsCount=1&arrival=2022-06-08&departure=2022-06-11&unitId=3160224brbrYour entire party will have plenty of space to relax- with 4950 square feet, 5 bedrooms & 4 baths. Architectural details like wide pine floors, 7 fireplaces & original wood beams, mixed with modern amenities such as massive kitchen with soapstone counters, 6 burner wood stove & post and beam great room with fireplace and french doors to the deck. Also just installed central AC which most homes on North Shore do not have!!!!brbrA few miles from famous Crane Beach, minutes to downtown Essex & famous fried clams and 10 minutes to Manchester-by-the-Sea and Historic Ipswich. This home truly has charm unlike any other vacation property you have stayed in. Come relax, enjoy and BE OUR GUEST!!!!! brbrWe also have a relationship w/an amazing local chef that can create a personalized dinner party/menu for your group. ABSOLUTELY spectacular experience and please tell her we sent you: Jamie Soucy jaimesoucy@gmail.com Inst: @jaimethinksaydobrbr***Typically we require a Friday and Saturday night stay and then you can add as many weeknights as you would like. This way the price for the home calculates properly. We do allow just weekday night stays but the price is higher than what the site will calculate. (typically 1000/nigh mid-week) Please email for specific rent for just weeknight but please understand the site will not calculate just weeknights properly. The rent when combined with 2 weekend nights (Friday and Saturday) will always calculate accurately though.brbr***Sorry no weddings or large parties are allowed at the house per town ordinance. Smaller parties or gatherings usually allowed but please detail your use of property before booking. thank you :)***
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Home Most popular vacation rentals in Essex

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Exceptional(51)

$137.62

/ Nightly
Private vacation home

The Little House+Walk to Essex Waterfront+BEACH

Essex, Massachusetts, United States

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Sleep 2

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Exceptional(51)

$360.79

/ Nightly
Apartment

Relaxing Rivers Edge Main Street Retreat

Essex, Massachusetts, United States

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Bath 1

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Sleep 6

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Exceptional(51)

$368.61

/ Nightly
Private vacation home

NEW - 2 bed / 2 bath+large Deck in the center of beautiful Essex, MA

Essex, Massachusetts, United States

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Bath 1

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Sleep 5

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Exceptional(51)

$544.54

/ Nightly
Cottage

Coastal Cottage on Private Island, overlooking the Essex Great Marsh

Essex, Massachusetts, United States

Bed 2

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Bath 1

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Sleep 5

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Exceptional(51)

$560.37

/ Nightly
Private vacation home

Winter deal! Charming 3-bedroom house on one floor in Essex

Essex, Massachusetts, United States

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Bath 2

Bath

Sleep 6

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Exceptional(51)

$601.66

/ Nightly
Cottage

Spacious Lakefront Escape w/ 3 Baths + Bonus Bed

Essex, Massachusetts, United States

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Bath 3

Bath

Sleep 6

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Exceptional(51)

$1720.18

/ Nightly
Private vacation home

Renovated Home with Private Pool

Essex, Massachusetts, United States

Bed 5

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Bath 3

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Sleep 10

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Exceptional(51)

$599.46

/ Nightly
Private vacation home

Winter deal! Delightful 3-4 bed one floor, 3 baths, fireplace

Essex, Massachusetts, United States

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Bath 3

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Sleep 10

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Exceptional(51)

$1200.92

/ Nightly
Country House

Rustic Luxe FarmHouse a Few Miles To Crane Beach: deck &jacuzzi overlooking pond

Essex, Massachusetts, United States

Bed 5

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(51)

$530.58

/ Nightly
Cottage

Modern Cottage, Private Island, Unparalleled beauty

Essex, Massachusetts, United States

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Bath 1

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Sleep 4

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