Vacation Rentals By Owner In Chatham, MA

$978.67

Classic Waterfront Chatham Estate

Chatham, Massachusetts, United States

Overlooking the Mill Pond, one of Chatham’s most scenic harbors, this property offers stunning vistas of both sunrise and sunset, and direct access to the water via a private dock.brbrConveniently located just steps from Main Street, this home provides easy access to all that downtown Chatham has to offer, eliminating the need for constant car travel. Within a mile radius, both Lighthouse Beach and Oyster Pond Beach offer enjoyable recreational opportunities.brbrThe residence consists of a traditional five-bedroom home designed in the classic Cape style, complete with authentic touches throughout, including antique furniture, a spacious porch with Adirondack chairs, side porch, an eat-in kitchen, lush grounds, and a private driveway. Smart amenities like WiFi, a cable TV, and a gas grill are also available. With easy access to Mill Pond, guests can enjoy activities such as kayaking (with rental delivery available), fishing, and convenient ferry service to Nantucket Island merely half a mile away.brbrIdeal for a family getaway or entertaining visiting friends and extended family, the main floor features a mix of formal and casual living areas, including a generously-sized patio with ample seating, and a barbecue area set amidst meticulously manicured lawns gently sloping towards the water's edge. Upstairs, the layout comprises five bedrooms, with a striking master suite complete with panoramic views. Available for weekly rentals, the refreshing summer breezes from the water provide a pleasant ambiance as you relax with your favorite drink and watch the bustling boat traffic. An outdoor shower completes the property after a long day on the water or exploring one of Chatham's many beautiful beaches.brbrThe advantageous location of this property allows for convenient access to town amenities, and the popular Lighthouse and Oyster Pond beaches, just a brief walk away. Explore the local dining scene, attend live band performances, shop around, and catch a Cape Cod League baseball match with a short stroll up the street.brbrDuring peak season, a seven-night minimum stay is required. brbrNon-refundable $500 Administrative fee, $695 Cleaning fee (Linens Included), plus applicable taxes (state and local taxes at a rate of 14.45% are applicable to all reservations under 31 days.)

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$317.58

/ Nightly

Cottage

Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views

Chatham, Massachusetts, United States

On over two acres of Oceanfront, 'Bayberry and Seadaisy Cottages at Ridgevale Beach face the temperate waters of Nantucket Sound. It is ideally situated at Ridgevale Beach and the mouth of 'Buck's Creek' a beautiful tidal estuary offering great swimming, boating, and shellfishing, as well as spectacular views. Shorebirds, from tiny Sanderlings to the Great Blue Heron, are frequent visitors. The Sundeck provides a relaxing spot for enjoying it all.brbrInside, each window frames a portrait of open ocean, river, or salt marsh. The cottage is heated, and comfortably furnished with fireplaced living room, full kitchen, two bedrooms, and bath. SMART CABLE TV, WIRELESS INTERNET, AIR CONDITIONING and outdoor gas grills and KAYAKS are also provided. In addition, the cottage has a private outdoor shower, a simple and delicious pleasure after a day on the beach.brbrWe are open year round, and between November and March, are treated to fantastic ocean sunsets! For summertime, reservations are necessary well in advance. The cottages are rented out by the week from Saturday to Saturday from June to the end of September. In the quieter off-seasons, we can often accommodate guests on short notice.brbrKeywords: Cottage

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$1402.02

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Private Vacation Home

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

Chatham, Massachusetts, United States

Ocean Harbor Waterfront. brbrStunning downtown Chatham Waterfront location with panoramic views, (Little Mill Pond) with beautiful, unobstructed views of both Little Mill Pond and Mill Pond, perfectly sited on the bank to take advantage of the ocean breeze. From the backyard overlooking the harbor, watch the boats come & go, walk down the private stairway to the harbor. Quiet, peaceful neighborhood.brbrFast WiFi, separate work space/home office and suitable for children. brbrAn easy walk to Lighthouse and Andrew Hardings Beaches. And a two minute stroll to Chatham Village's quaint shops and restaurants. The home is in a peaceful, quiet neighborhood which is only a short stroll to go to Chatham Village on Chatham's Main Street. An easy walk to Lighthouse Beach from the house, or to Chatham's Fish Pier, each about a 15 minute walk. Bring or rent your kayaks or paddleboards from the dock within view of the house or bring your boat. This is the perfect water view, in-town location to enjoy everything that makes Chatham a perfect getaway destination for you, your family and your friends. brbrPLEASE NOTE, WE DO NOT ACCEPT NOR WOULD WE EVER REQUEST ANY TYPE OF WIRE TRANSFER WHILE MAKING YOUR RESERVATION. IF YOU RECEIVE A REQUEST TO MAKE A WIRE TRANSFER FOR RESERVING THIS OR ANY OTHER PROPERTY, PLEASE CONTACT HOMEAWAY'S SECURITY DEPARTMENTbrbrCompletely renovated-- 4-1/2 Bedroom Home (1 on the first floor) with 3 full baths, a custom kitchen, central A/C, gorgeous wood floors, brick walled patio, Anderson windows, new stainless steel appliances, all new furnishings and a huge ocean-front backyard with private stairway access to the ocean harbor on Little Mill Pond. Steps from downtown and a short walk to Lighthouse Beach and Andrew Hardings Beach. Unique in-town location where you can live on the water and walk into quaint Chatham Village’s unique restaurants and shops! Sleeps 12. Both of the Living Room areas, the dining room, and three of the four bedrooms have amazing waterfront views. Come and enjoy your quiet, private, oceanfront retreat and enjoy the beaches and Chatham Village's Main Street, only steps away! Or simply stay without needing to leave the house or outdoor spaces while relaxing and enjoying the panoramic views.brbrHome was featured by Eileen Cotter of Pure Wander, and here is her Video Walkthrough:brbrhttps://www.youtube.com/watch v=_tqi6m8-1zs&tbrbr

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$1801.14

/ Nightly

Private Vacation Home

Panoramic Water Views w/ Private Beach!

Chatham, Massachusetts, United States

Summary:brbr16684 - Deja View: Panoramic Water Views w/ Private Beach!brbrbrbrThe Space:brbrFind yourself on island time at this exclusive private association home in one of the most prestigious Chatham neighborhoods, this vacation retreat presents an unparalleled coastal escape. Gazing over Chatham Harbor with the grand corner windows throughout, the property boasts a sprawling grassy yard, great for family fun in the sun and a uniquely crafted architectural gem that seamlessly marries comfort and style. Recently treated with a tasteful redecoration, the interior unfolds with a splendid layout designed for both seclusion and relaxation. *Please note the staircase to the ground floor is a metal, spiral staircase. Almost every room offers breathtaking views, and the main level orchestrates the pinnacle of privacy for couples or families, with bedrooms situated at opposite wings, each accompanied by its own well-appointed bathroom (not en-suite).brbrStep down your private staircase directly onto the pristine sands of Chatham Harbor for a serene beachfront experience. Immerse yourself in the beauty of sunsets as you savor cocktails and engaging conversations in the expansive living area or on the back deck, both commanding panoramic water views. A mere 5-minute drive brings you to the iconic Chatham Lighthouse, while the vibrant charm of downtown Chatham Main Street beckons just 2 miles away. Culinary delights await at Bluefins Sushi Bar, and for those seeking lively nightlife, the renowned Chatham Squire is within easy reach. Indulge your sweet tooth at Chatham Candy Manor, where homemade candies promise a delightful treat for the entire family. Your idyllic Cape Cod getaway begins here, where luxury and convenience converge in perfect harmony.brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 10brBedroomsbr-Total 5br-1st Floor - 1 King Bedbr-1st Floor - 1 Queen Bedbr-Ground Floor - 1 Queen Bedbr-Ground Floor - 1 Queen Bedbr-Ground Floor - 2 Twin BedsbrBathroomsbr-Total 3br-1st Floor: Showerbr-1st Floor: Showerbr-Ground Floor: ShowerbrOther Amenities br-2 Blue single person kayaks are available for guest usebr-Central ACbr-WiFibr-TVbr-Washer/Dryer br-Propane Grill br-Please note outdoor amenities are available seasonallybr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade Disinfectantbr-Parking for 4 cars maximumbrC0463510550brbrbrbrOther Things to Note:brbrPlease note the staircase to the ground floor is a metal, spiral staircase.

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$1003.27

/ Nightly

Private Vacation Home

Newly Remodeled Seaside Getaway with Forest Beach in your backyard!

Chatham, Massachusetts, United States

Newly renovated home with ocean views and Forest Beach right in your backyard. Swim, lounge, kayak, hike, or play tennis in the quaint neighborhood. Or venture to downtown Chatham for local shops, fresh seafood and night life!brbrIn the home:brNewly remodeled home has it all. Inside, have game nights in the cathedral ceiling living with a gas fireplace. Or, watch your favorite shows in the family room. A renovated kitchen and wet bar is also at your disposal. In your bedrooms, there is a bed and desk so you can work from home during your stay. brOutside, grill up a feast at the outdoor kitchen and enjoy the ocean views from the porch. There is an outdoor shower to rinse off at after a day at the beach!brbrIn the neighborhood: brIn a few steps (5 min walk), you can be lounging on the shores of Forest Beach or take a relaxing stroll through the trails of the Forest Beach conservation area. There is a public playground, tennis and basketball court in the cul-de-sac about 15 min walking. The kayak launch is located a 20 min walk from the property.brbrIn Chatham & beyond:brFor those in search of outdoor activities outside of our beautiful neighborhood, the Cape Cod National Seashore and Monomoy National Wildlife Refuge are both a 20 min drive away. Golf courses, parks, and surfing beaches are all within 10-15 min drive.brLooking to explore the local towns of Cape Cod Downtown Chatham is 10 min away offering local shops and bites. Provincetown is 50-min away and is perfect for a day trip!

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$1942.43

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Private Vacation Home

Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room

Chatham, Massachusetts, United States

About this spacebrWelcome to a beautiful Coastal retreat! — a spacious seaside escape perfect for families or groups. Steps from the beach, Main St & Chatham Bars Inn, this elegant 10-bed retreat blends comfort, fun, and Cape Cod charm.br*0.4 mi to beach, 0.5 mi to charming Main St & Chatham Bars Innbr* Tranquil front porch & lawn with kids’ playsetbr* Game room: pool table, Apple TV, gamesbr* Open-concept living with stunning 2-story glass wallsbr* Full kitchen, laundry, fast WiFibr* 10 beds + soundproof divider setupbrbrThe spacebrEscape to Coastal Haven, where sophistication meets family-friendly fun. Picture yourself enjoying sunny mornings on the porch, lively afternoons in the game room, and cozy evenings sharing drinks on the lush lawn. Ideal for multi‑generational stays or reunions, it caters to couples, families, or friend groups craving comfort, entertainment, and unforgettable gatherings. With sleep setups tailored to your clan and easy beach-town access, every stay feels effortlessly luxurious and thoroughly fun.brbrWelcome to this 7-bedroom, 4-bathroom seaside home that accommodates up to 14 guests—perfect for family vacations, group getaways, or corporate retreats.brbr* Sleeping Arrangements:brbrMaster Suite (1st floor): King bed, ensuite bathroombrbrGuest Room (1st floor): Queen bed, full bathbrbr2nd Floor: Two large rooms convertible into four with sound‑proof walls—six twin bedsbrbrGround Level Bedroom: King bed + couch, sliding access to front lawnbrbrLiving Room: Sofa bed / folding mattressbrbr* Living & Dining Areas:brbrOpen-concept living with 2-story ceilings and full glass wallsbrbrSpacious sectional couch and smart TVbrbrDining sets seating 8+ at table and bar seating for 4brbrFully equipped kitchen with stove, oven, dishwasher, coffee maker, and morebrbr* Bathrooms:brbrBathroom 1: Ensuite in master—spa-equippedbrbrBathroom 2: Full shared bath (1st floor)brbrBathroom 3: Ground-level full bath adjacent to laundrybrbrBathroom 4: Shared upstairs bathbrbr* Entertainment & Amenities:brbrGround-level game room: pool table, Apple TV, puzzles, gamesbrbrFront porch with seating overlooking lawn and kids' playsetbrbrBackyard with plenty of space with a large lawn, hammock, spike ball - open flames and firepits are not permitted.brbrLaundry room, high-speed Wi‑Fi, parking for up to 6 carsbrbrNestled in the heart of Chatham, just 0.4 mi from the beach and 0.5 mi from Main Street and Chatham Bars Inn, Coastal Haven offers an unbeatable location.brbr* Top Attractions Nearby:brbrChatham Lighthouse – historic beacon with scenic dune viewsbrbrChatham Fish Pier – watch local fishermen, seals & savor fresh seafoodbrbrHarding’s & Lighthouse Beaches – sunbathing, swimming & sunset walksbrbrAtwood House Museum – a look into 18th‑century Chatham and maritime lifebrbrMonomoy National Wildlife Refuge – birdwatching and peaceful trailsbrbrBeyond these, enjoy boutique shopping and dining on Main Street, family baseball games at Veterans Field, and seasonal shark or wildlife cruises. With beaches, history, and coastal charm steps away, your perfect Cape Cod escape awaits!brGuest accessbrWhen booking this house, it is all yours. Enjoy the large front deck, the smaller deck out back, and a huge front yard with play set for the kids. You'll find peace and comfort in this quiet private setting in the best location in Chatham.brbr** Places of Interest Within Minutes of House **brbrMain Street - Shopping, art galleries, restaurants (0.5 miles)brFish Pier - Watch fishermen land today's catch, then buy it (0.7 miles)brOyster Pond Beach - One of several kids' beach (1.1 miles)brCape Cod Bike Trail - Trail and bike rental (1 mile)brCommunity Center - Indoor b-ball, kids' game room (1 mile)brbrBeaches to walk or drive to:brHaloway/Lighthouse Beach (no fees, 0.2 miles)brChatham Bars Inn (CBI) or Caflin Beach (.5 miles)brScatteree Beach (salt water fly fishing, no fee, 2.0 miles)brNorth Beach (by boat, swim, surf, surf casting & fly fishing, 1 mi)brLighthouse Beach (surf casting, no fees, ltd parking, (0.5 miles)brMany others within 4 mibrbrGolf: Seaside Links 9 hole, public course by CBI (0.7 mi)brCaptain's Course (36 holes)brEastward Ho! Country Club (private)brCape Cod National (private)brbrSpas: CBI, Sol Spa, Le Petite Day Spa (0.7 to 2.0 miles)brTennis: CBI, Wequassett Inn, Chatham Public Courts (0.7-1 mi)brbrFriday night band concert downtownbrChatham A's Baseballbrbr** Airport and Transportation Info **brbrBoston/Logan Airport 91 milesbrProvidence/TF Green Airport 101 milesbrHyannis Airport 21 milesbrChatham Airport (CQX 3,000' runway) 2.1 milesbrHarwichport Ferry to Nantucket 7.4 milesbr brKeywords: Chatham, MA Rental, Private, clean, family rental, convenient, fishing, beaches, Golf, spa, downtown Chatham, green, pleasant, ocean,

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$277.95

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Cottage

Chatham Cottage on the Big Pond One Mile to Ocean Beaches

Chatham, Massachusetts, United States

Get away and relax at our cottage on White Pond in beautiful Chatham Cape Cod. The cottage has a private fresh water beach, canoe, kayak and row boat. Harding salt water ocean beach is one mile away. Fishing, golfing, bike trails and downtown Chatham are minutes away.brbrRelax in your bedroom with full size bed, private bath, screened in porch and streaming TV. Your children have their own room with two bunk beds, a twin bed, bath room, TV and a private screen porch. brbrAfter a day at the beach you can clean up in the outside shower, barbeque your favorite dinner, eat on the deck or just enjoy your favorite beverage. There are six acres of private open area on the pond if you want to take a walk or your children want to ride their bicycles and unwind.brbr2025 SUMMER SEASONAL RENTAL JUNE, JULY & AUGUST ALSO AVAILABLE. PLEASE CONTACT OWNER.br br br br brbr

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$302.47

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Apartment

Cape Cod Chatham Water View Retreat

Chatham, Massachusetts, United States

Secluded Cape Cod Chatham retreat on tidal estuary creek. Conservation land assures privacy. Easy and safe private entrance from level flagstone patio. Quiet large designer studio with queen bed, large stone fireplace and French doors opening to private patio. Plus a sitting area with sofa bed and spacious dressing room and lavish oversize bath. Ideal for a or couple or three persons. No smoking or pets. Three day minimum rental. This serene property will bring you close to remembering and enjoying the Cape of olden days. No expense was spared in developing this finely detailed space.

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$616.27

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Private Vacation Home

Pleasant Chatham Cape

Chatham, Massachusetts, United States

Pleasant Chatham Cape - A Classic Cape Cod Getaway with Modern Comforts brWelcome to Pleasant Chatham Cape, a charming 4-bedroom vacation rental that perfectly blends classic Cape Cod charm with modern amenities. Nestled between Chatham and Harwich Port, this home is ideal for families, pet owners, and beach lovers looking for a relaxing escape. With a fully fenced backyard, spacious deck, fire pit, and bikes for exploring, your perfect Cape Cod getaway awaits.brPrime Location – Walk to Everything!brPleasant Street Beach – Just a 10-minute stroll (0.7 miles)brWalk to Drifters & Pisces, two highly-rated local restaurantsbr~5 minutes to Harwich Port and ~10 minutes to Downtown Chatham – boutique shopping, seafood, and morebrEasy access to the Cape Cod Rail Trail – explore 25 miles of scenic biking and walking pathsbr5 minutes to groceries and gas – convenient for stocking upbr Chatham Vacation Home – Key Featuresbr4 Bedrooms | Sleeps 6 comfortably (2 Queens, 4 Twins – including a bunk bed) NOTE: As is common on Cape Cod, Guests are responsible for providing their own linens, including sheets and towels, at this property. br1 Full Bathroom + Outdoor Shower (seasonal) – Ideal for post-beach rinse-offsbrFully Equipped Kitchen with a 6-burner gas range - Stocked with cookware, modern appliances & a ****dual coffee makerbrCozy Living Room – Smart TV, board games & books for a relaxing staybrHigh-Speed WiFi for streaming & remote workbrOutdoor Fire Pit & Seasonal Outdoor ShowerbrSpacious Deck with a Gas Grill & Dining AreabrFenced Backyard – Pet Friendly! (1 Dog Considered)brCentral Heating/Air Conditioning – Stay cool in the summer & warm in the winterbrFull Washer & Dryer – Pack light & refresh your clothes during your staybrBikes Available – Ride the Cape Cod Rail Trail straight from the housebrBeach Chairs + Umbrella – Access to 6 beach chairs and an umbrella so you don't need to BYObr Sleeping Arrangements + BathroomsbrThe home comfortably sleeps 6 guests (with flexible arrangements for up to 8).brFirst Floor: 1 Queen Bedroom and 1 Twin Bunk Bedroom (Ideal for Kids)brSecond Floor: 1 Queen Bedroom and 1 Loft-Style Room with 2 Twin BedsbrBathrooms: 1 Full Bathroom (Shower) on the First Floor and 1 Full Bathroom (Tub) on the Second FloorbrBonus: A seasonal outdoor shower – a must-have for beach daysbr Fully Equipped Kitchen + Outdoor DiningbrWhether you're cooking a gourmet meal or grabbing a quick bite before heading to the beach, our well-stocked kitchenhas you covered.br6-Burner Gas Range & OvenbrDual Drip + Keurig Single-Serve Coffee MakerbrCookware, Utensils, & Spices ProvidedbrIndoor Dining Table for SixbrOutdoor Deck with Gas Grill & Dining Areabr Relax, Unwind & Explore the OutdoorsbrAfter a day at the beach or exploring Cape Cod, enjoy your private backyard retreat:brGather around the fire pit for s’mores under the starsbrTake the bikes and explore the scenic Cape Cod Rail TrailbrRinse off in the outdoor shower after a fun day in the sandbrLet your furry friend roam safely in the fenced-in yardbr Bringing a Dog Here’s What to KnowbrWe welcome one pre-approved dog per stay. A $150 pet fee applies.brDogs must stay off the furniture and bedding. If your dog is used to being on the sofa or bed, please protect the furniture with appropriate coverings.brService and ESA animals must be disclosed prior to booking. Pet Fee is waived only for legitimate service or emotional support animals in which the animals are never left behind without the owner. Evidence that the animals were left behind will result in the pet fee being charged.br Important NotesbrNo smoking or parties allowed on the property.brPrimary renter must be at least 25 years old to book. A valid photo ID is required prior to check-in.brAs is common on Cape Cod, Guests are responsible for providing their own linens, including sheets and towels, at this property. Pillows, blankets and covers are provided. Guests can bring their own or we refer to Chatham Concierge for linen services where you can rent from their online store. They can deliver linens to the property on your arrival date and pick them up on your departure date. The cost for linen rentals varies depending on your needs and planned occupancy.brA rental contract must be agreed to during the booking process. The Guest is responsible to read and understand the rental rules prior to booking. By clicking Request to book the Guest is accepting all of the terms and conditions.brThis home is on a septic system so occupancy is strictly enforced to avoid a septic backup of sewage in to the house. Your max occupancy during your booking is what you submit in your booking. Additional guests must be approved.brCheck-out time is strict, and if our cleaners arrive while you're still at the house, we may incur extra charges, which will be passed on to our guests.brWe are not responsible for any injuries, illnesses, or accidents that may occur during your stay, nor for the loss of personal belongings or valuables.brFireplace in living room is decorative only.brA Trust + Safety Fee is applied per night in lieu of a security deposit.br ★☆ Book Now & Let Us Host You at Pleasant Chatham Cape! ☆★br Follow & tag us on Instagram: @pleasantchathamcapes

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$402.05

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Private Vacation Home

5BR-Beautiful Chatham-Year Round-Sleeps up to ten (10) & 1 Mile to Town!

Chatham, Massachusetts, United States

My family and i live full time in lexington, ma. We decided to purchase a vacation home in chatham, ma because of the short access from boston. Chatham has all the charm and beauty as nantucket island has which is where we married. It just so happens chatham is so much easier to get to than nantucket! This was an investment for us as we enjoy the experience and the quality of life we have had vacationing in chatham. It is a wonderful vacation spot and best on the cape! We hope you enjoy your stay!brbrKeywords: beautiful year round vacation home with finished hardwood floors throughout - totally renovated with a beautiful exterior deck and covered eating area. New yard, new siding, new deck, new irrigation system, new hardwood floors, new recessed lighting, new beds, newly painted walls, new furniture and all the appliances. Includes new HVAC heat and central a/c throughout for those humid days/evenings!brbrGiant deck in fully fenced in backyard takes full advantage of both sun and yard area. Spring, summer & fall seasonal ping pong table, above ground fire-pit, horseshoes, and fenced in hot/cold outdoor shower - all new!!!. brbrBeach chairs (6+) and bikes (2+)brInclude cooler/wheels and beach trolley (other kids beach items) huge stainless steel gas grill. brbrFifth bedroom located with separate exterior entrance off of back deck for folks that want some extra privacy!brbrWe have five property's in Chatham, MA at ChathamVacationProperties.com brbrLinens & towels not included (pillows & blankets are included)

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$476.88

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Private Vacation Home

Charming Air Conditioned Chatham Vacation Home Walk to Beach & Tennis

Chatham, Massachusetts, United States

This charming house is located on a landscaped, level lot on a quiet, dead end lane just 4/10 mile from Forest Beach on Nantucket Sound. The house has a lovely bedroom with a queen size bed, a tiled bathroom, a beautiful kitchen, a dining area opening to a large deck, a living room with a fireplace and French doors opening to a delightful screened porch on the first floor. The upstairs has three charming bedrooms, two of these bedrooms have 2 twin beds and the other has a queen size bed. There is a full size tiled bathroom on the second floor as well. The house has cable HD TV, a DVD player, high speed wireless internet, an enclosed outside shower, a barbecue, beach chairs and central air conditioning and heat. A town tennis court and the bike trail are a short walk away. Chatham is one of the most beautiful towns on Cape Cod that offers beaches, golf, great dining, unique shopping, seal watching, biking and water sports. leases made from July 1st 2019 onward will have the tax of 12.45%

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$1018.27

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Private Vacation Home

Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond

Chatham, Massachusetts, United States

A charming 3 bedroom, 2.5 bath cape with large kitchen and private backyard, patio and deck that abuts conservation land. Located on a dead-end, tiny and quiet lane in the center of town just off Main Street in quaint Chatham village. brbrWalk to shops and restaurants. Oyster Pond beach (0.2 mile / 6 min walk). 1 min walk to Viera on Main bar and restaurant. Chatham Squire a 6 min walk. Lighthouse Beach a 20 min walk, less than a 5 min drive. Chatham A's ballpark an 8 min walk. All beaches with in a 10 min drive.brbr2026 ratesbrOff Season: Sept 30 - May 31: $750 per night 4 night min. $5,250 per weekbrSpring: June 1 - June 30: $5,978 per week (7 night min)brSummer: July 1 - Aug 31: $6,405 per week (7 night min)brFall: Sept 1 - Sept 30: $5,978 per week (7 night min)brbrCleaning Fee is $250 plus a security deposit is required. A complete linen package, including bed making and stripping is provided. Call to confirm rates and availability. Mass tax is 14.45%. brbrSecurity FeaturesbrTo enhance safety and protect the property, there is one outdoor security camera with a sensor spot light mounted above the garage entryway. It is motion-activated for light and camera and records only the exterior approach to the house (driveway) and is marked and can be switched off inside the home if renters prefer.brbrAlso, please view our next door 4 Bedroom cottage. VRBO listing: 108402. 4 night min in off season.

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$924.52

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Private Vacation Home

Stroll Chatham's Historic Downtown / Shops, Dining, Galleries, Etc.

Chatham, Massachusetts, United States

Beautiful home located in the heart of Chatham! This lovely home offers all the amenities and decor of a modern house while keeping the charm and character of a true Cape Cod. Spend your vacation just steps from the many shops and restaurants of Chatham's quaint downtown village or beautiful Lighthouse Beach. It sleeps 6 in three bedrooms, with three full baths. It is the perfect spot...start making your family's vacation memories right here, in the heart of Chatham!brCentral Air, Wireless Internet and 5 TV's: Sun-room, Livingroom and all 3 Bedrooms.

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$2042.93

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Private Vacation Home

Oceanside Chatham / 20% Reduction / July 6-11 ONLY

Chatham, Massachusetts, United States

brWe have July 6-11 (ONLY) now available at a 20% reduction. The Calendar pricing has been reduced to reflect the lower price. BOOK NOW. brbrThis exquisitely furnished, charming Cape Cod house is within an easy walk of Chatham's beaches, Fish Pier, Lighthouse, Town Center, outdoor Band Concerts, spa, and fine restaurants. We have deeded rights to water via our private path. 4 swimming beaches are within an easy walk. brbrIt's just a few minutes' walk to The Chatham Bars Inn, golf, spa, tennis facilities and world-class restaurants. brbrThe home sits on nearly an acre (double lot) and has a huge back yard with organic vegetable and flower gardens. The home is well equipped and well maintained and is situated in what is perhaps Chatham's most desirable location, just a short walk to the Chatham Light and Beach. brbrFishing, whale watching, boating, and ferries to Nantucket/Martha's Vineyard are all available nearby.brbrBedrooms include a master with Sleep Number split-king, and second bedroom with oversized twin set. Bedrooms three and four have trundle twins. brbrOn the property, we have the main house, garage, workshop, rusting bedroom at the side of the garage (teens and preteens), garden shed. We also have a historic windmill (under restoration, vacant, and not part of any rental).brbrWe have nearly all 5-star reviews, with well over a decade of hosting small families. brbrWe are happy to provide further information and answer any questions you may have.

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$629.48

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Private Vacation Home

AC, Pool, Hot Tub, Fenced Yard, Beach vacation home

Chatham, Massachusetts, United States

Spacious four bedroom, two bathroom, single family home with central air, above ground pool, hot tub, fire pit, and fenced yard, and located just 1.5 miles to Ridgevale Beach. Newly purchased and updated including brand new flooring upstairs, all new furniture including beds and mattresses, and new living and dining room.brbrStep right in to a bright open living room with plenty of couch seating for all of our guests. An open floor plan leads you into the kitchen with stainless steel appliances and a small table for in kitchen eating. A pass through leads to the dining room with seating for 8 as well as an additional table for our smaller guests. Downstairs features two bedrooms: one with a queen bed and the other with two twin beds as well as a full bath with tub. Upstairs features an additional two bedrooms: one with a king bed and another queen room as well as a bathroom with shower stall.brbrWhile the inside has been completely transformed, don't miss the amazing exterior of this vacation home! There is a large above ground pool, hot tub, and outdoor shower to enjoy after returning home from the beach. Home is on a quiet dirt road but nearby to easy access to Ridgevale Beach and all Chatham has to offer. Volunteer Park across the street has a skate park as well as a playground. Hop right on the bike trail across the street for a short ride to the airport or downtown Chatham with access to the Cape Cod Rail Trail.brbrLooking for a place to get away from it all Step right into this relaxing newly updated vacation home in a prime Chatham location with a private pool and hot tub as well as a short distance to Ridgevale Beach and Cape Cod rail trail bike path. Dip in the pool Check. Short drive to the beach Check. Walk to the pond Check. Large fenced in yard Check. Look no further than this updated home with a large back deck, outdoor shower as well as plenty of yard space to run and play. With three floors of living including four bedrooms, two full baths, and a game room in the basement, there is plenty of room for everyone. Across the street is a large park with a skate park and playground for kids. Whether you are looking for a weekend away with friends or a summer vacation with your family, this home has it all.brbr*Please note that the owner has installed two outdoor security cameras on the front of the property

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$512.54

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Private Vacation Home

Charming Chatham House Walk to Downtown

Chatham, Massachusetts, United States

We make it easy to plan your vacation on Cape Cod in Chatham, MA. This well-appointed, renovated home is centrally and conveniently located to all that Chatham and the surrounding towns have to offer. Enjoy the downtown Main Street Old Village with restaurants and shops plus beaches, Fish Pier and Cape-league baseball only a short stroll away. When you return for the evening enjoy the patio, grill out or just relax in front of the flat screen TV and watch your favorite movie. There are also bikes for a ride on the bike path or to Light House Beach.brbrThe house has central AC, washer and dryer, a refrigerator with ice maker, dishwasher and outside shower. On the main level, there is a king bedroom with king-sized bed, double closet and en suite bath with shower. Second and third bedrooms include one full bed and two twin beds, respectively, both with double closets. There is also another full bath with tub and shower. The comfortable living room includes two couches and a flat screen TV while the lower level features a family room with TV and a bunk room that sleeps 2 in bunk beds. Enjoy your meals or a game of cards in the dining room. Or, take in those beautiful Chatham nights outside on the patio with gas grill plus fire pit.brbrAnd because we know that packing and travel can be a headache, we start you with the basics. You’ll find much of what you need upon arrival including: Linens, Bath and Beach Towels, Beach Chairs, Bikes w/Helmets and High Speed Internet. We even provide many household staples to get you started – Paper Towels, Toilet Paper, Soap, Laundry Detergent, etc. just so you don’t have to bring it all with you or make a grocery run. Rather, you can begin enjoying all that Chatham and 137 Shane Drive have to offer upon arrival!

Bed

Bath

Sleeps

$545.6

/ Nightly

Private Vacation Home

Relaxing 3br, private yard, walk to beach, close to bike trail and shopping!

Chatham, Massachusetts, United States

Relax and unwind at this charming South Chatham cottage, just a short 0.4-mile walk to Pleasant Street Beach. Set on a large private lot, this home offers the perfect blend of classic Cape Cod charm and modern updates—ideal for a laid-back coastal getaway.brbrInside, you’ll find a bright, open-concept living and dining space designed for easy gathering after a day at the beach. The fully renovated kitchen is well-equipped for cooking at home, and the updated bathrooms and in-unit washer/dryer make your stay comfortable and convenient. Air conditioning is provided via slim-line wall units.brbrThe home comfortably accommodates families and small groups with three bedrooms:brbr* First floor: one bedroom with a twin plus twin trundlebr* Second floor (accessed via spiral staircase): one bedroom with 3 twin beds, and one (split) King bedroom brbrThe full bathroom—newly renovated with a walk-in shower—is located on the first floor, while a half bath is located upstairs.brbrPlease note: the spiral staircase adds character but may not be ideal for very young children or guests with mobility concerns.brbrThe outdoor space is a highlight of the property. Enjoy morning coffee or evening drinks on the front deck overlooking the spacious yard. After the beach, rinse off in the enclosed outdoor shower, then grill dinner and relax outside. Beach chairs and toys are provided so you can fully enjoy your time by the water.brbrLocated in a quiet South Chatham neighborhood, the home offers both privacy and proximity—walk to the beach, and a short drive to shops, restaurants, and all that Chatham has to offer.brbrPerfect for: families, beach lovers, and small groups looking for an easy, relaxed Cape Cod escape with space to unwind.brbrAdditional Details:brParking for up to 3 cars is available in the driveway (no garage). Bed linens and bath towels are provided; guests should bring their own beach towels. Propane is provided for the gas grill. Slim-line/window A/C units provide cooling in main living and sleeping areas.

3

Bed

1

Bath

7

Sleeps

$706.92

/ Nightly

Condo

Steps to Chatham's Historic Downtown

Chatham, Massachusetts, United States

Luxury Retreat on Popular Main Street Chatham. This unique hide-a-way is a spacious 2 bedroom 2nd floor condo in the heart of Chatham Village. This unit has its own private balcony. This rental is carefuly furnished with comfortable furnishings, high end kitchen & baths, right down to the decor. Spend your vacation just steps from the many shops and restaurants of Chatham's quaint downtown village or beautiful Lighthouse Beach. It sleeps 4 in 2 bedrooms, with two full baths. It is the perfect spot...start making your family's vacation memories right here, in the heart of Chatham! brCentral Air & Wireless Internet

Bed

Bath

Sleeps

$684.19

/ Nightly

Private Vacation Home

The Boarding House, King bed comfort. Close to Nantucket Sound beaches.

Chatham, Massachusetts, United States

This completely renovated 4 bedroom cape is less than 3 miles from Nantucket Sound beaches. Inside there is central air conditioning. It features 2 extra large king bedrooms and a half bath upstairs and one king bedroom, one twin bedroom and full bath downstairs. The kitchen is completely redone with new appliances, cabinets, and granite counter tops. The living room has a leather sectional and a new 55 OLED TV. Outside there is an amazing outdoor shower, a spacious deck with built-in mahogany seating and an 8 foot shaded picnic table where you can enjoy your meals. The back yard is an oasis of ornamental trees and shrubs that give the area a cool airy feel. There is a shed in the back for guests to keep their bicycles and beach chairs. The bike path is about 300 feet from the house, accessed by a small trail at the end of the street. After the beach (or whenever you like!) you can enjoy delicious homemade ice cream from the shop 2 doors down. There are a number of excellent restaurants less than 3 miles away. The town of Chatham is 3 mile east and Harwichport is 3 miles west. The front yard is enclosed by tall hedges, and is a great place to see the clouds turn colors at sunset.

4

Bed

1

Bath

8

Sleeps

$956.76

/ Nightly

Private Vacation Home

Relaxing Cape Escape • Family Retreat • Walk to Beach • 6 beds • Sleeps 8

Chatham, Massachusetts, United States

Tucked between Forest Beach and Pleasant Street Beach, Stone’s Throw is a light-filled 4-bedroom, 3-bath South Chatham retreat ideal for families or couples traveling together. Vaulted ceilings and a bright sunroom create an easy Cape feel, two bedrooms on the main floor feature private en-suite baths while the lower-level bedroom includes a 3rd full bathroom across the hall. Maximized for comfort and privacy. Walk to Forest Beach, bike to Red River Beach, and enjoy evenings grilling at home or dining nearby at local hot spots like Buca, Dive and many others. New listing with updated furnishings and professional photos coming soon.

4

Bed

3

Bath

8

Sleeps

Vacation Rentals By Owner In Chatham, MA

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