Vacation Rentals By Owner In Westport, MA

This 3 bedroom, 2 bath beach cottage is located in desirable Westport Harbor just a minutes walk from the beach! Central air conditioning in the main house is perfect for those hot summer nights, or you can enjoy the ocean breeze! The spacious back deck with conversation seating overlooks an open backyard-perfect for relaxing and enjoying the oceans sounds. There are two smart TVs, one in the main living room and one in the 3 season room complete with a video library. The cottage is great for a small family vacation getaway!

Cozy Beach Cottage- walk to beach

Westport, Massachusetts, United States

Bed

Bath

Sleeps

$216.7

Visiting the Farm Coast Why not stay on a Farm! The Swift's Nest is a guest house located on our working farm and garden. The studio apartment is private and accessed by a farm lane that will take you past our apiary, orchard and wildflower gardens. Located above our honey room, this generous studio enjoys exceptional views. Distant winter views of the Westport River are replaced by a bright pastoral of wildflowers, hayfields, and forests in the summer. Come enjoy and relax.brbrThe Swift's Nest is a guesthouse located on our 5 acre farm and garden in Westport just across the road from the Westport River. The guesthouse is located above our honey room where we store beekeeping equipment. It is accessed by a private exterior stairwell leading to a second story deck with amazing views of the farm and beyond. The guesthouse is private from the primary home and enjoys separate access from the road. Plenty of room for parking, including boat trailers. Easy trips to the beaches, boat ramps, conservation land, Buzzards Bay Brewery, Westport Rivers Winery and more. The studio apartment has one king bed. Additional sleeping arrangements for those traveling with children including porta-crib and child bedding available on request.brbrWe named the guesthouse after the resident Swifts that live in the old chimney in the adjacent workshop. The farm is a birders paradise and a dream for wildlife enthusiasts. We encourage guests to tour our gardens and share in the bounty of flowers and food that we produce here for our family. Please note: this is working apiary, and we can have anywhere from 5 - 15 hives of honeybees at any given time. The honeybees are located about 150yards from the guesthouse, a safe distance for those who aren't inclined to be up close and personal with bees. We invite guest to exercise caution around the bees and keep their distance. If you're interested in the bees and want to take a closer look (or taste) please let me know and we can coordinate a tour.brbrYour stay is helping us restore the 100-year-old greenhouse on the property. Thank you.

Apartment

Studio guesthouse on our farm in beautiful South Westport.

Westport, Massachusetts, United States

Bath

Sleeps

$1188.81

Please note: we rent our guest house for only 14 nights a year and 2026 is already fully booked.brbrOur guest house is located on the banks of the Westport River down a secluded dirt lane, within a 3 minute walk to a private sandy beach and dock. This is the perfect getaway for families with young kids looking for an idyllic beach/country vacation they will never forget. The house was built in 2025 and is used mainly for our friends and family but we do rent it on a very selective basis when it's available. It's finished to a very high standard, and includes new appliances, furniture, bedding, kitchenware, towels, and anything else you might need in each room.brbrThe blue bedroom is on the top floor (we call it the penthouse suite) and that floor also has a large living and dining area, kitchenette, bathroom and balcony with outdoor furniture. Also on this floor is the “Kid’s Cwtch” which is a small area set up to be used by smaller kids for playing and sleeping with a couch/futon and their very own TV. We’ve had a 3 kids sleep there very comfortably. The Yellow Bedroom has a queen bed and a couch/futon that can sleep two bigger kids. The green bedroom has a king bed only, and the bunk room has 3 bunk beds that will comfortably sleep 6 adults.brbrOutside, there is plenty of parking and lawn for playing, and there is a veranda, deck and patio with lots of outdoor furniture for dining or simply relaxing, with umbrellas to provide shade and a large firepit with space for everyone to sit around.brbrOptionally, with a signature of our association temporary membership and a $400 fee, you have access to a private sandy beach which has safe swimming and access to a launch ramp and dock. We have three kayaks available for your use at your own risk, but if you want to bring a bigger boat for mooring or temporary dockage that can be arranged for an additional fee.brbrWe are 10 minutes walk from Buzzards Bay Brewery which has many events and food trucks on it's park-like setting and 5 minutes drive from Westport Rivers Winery which has events, fire pits and food trucks overlooking the vineyard. A 15 minute drive gets you to Horseneck Beach and multiple restaurants.brbrBecause we rent our guest house rarely and selectively, we have not posted interior photos but we can provide them and answer any questions before you book. Please tell us about yourself and your party to get the best chance of being accepted as our guests.

New 5-bedroom house with secluded yard, deck & access to private beach & dock

Westport, Massachusetts, United States

Bed

Bath

Sleeps

$311.17

Brand new renovation, located on the Westport River's east branch. This west facing charming 3 bedroom is perfect to enjoy sunsets. Close to beaches, the quaint Westport downtown, a brewery, winery and 10 minute drive to Dartmouth. This 3-bedroom house in Westport is perfect for your escape to relaxation. With 2 queen beds and 2 twin beds in a private neighborhood, this lovely property offers a serene atmosphere for guests. Kickback, relax, and enjoy everything Westport and our house has to offer.

Newly renovated, 3-bedroom house in Westport with gorgeous waterfront views

Westport, Massachusetts, United States

Bed

Bath

Sleeps

$295.21

Charming cottage in the historic district of Westport Point. Master bedroom with queen bed. Smaller bedroom trundle bed (2 twins) and removed guest house with two twin beds. A huge yard is visited by many varieties of wildlife. A back screened-in porch is perfect for meals or reading. A private hideaway perfect for couples or a small family. Stroll to the wharf to view the sunset or drive/ride 2 miles to Horseneck beach, Gooseberry Neck or the Audobon Bird Sanctuary. A mix between farm and beach, Westport's 1 hour drive from Boston makes it a favorite for those who want the feel of Cape Cod without the traffic headaches. The area is popular with cyclists and culinary enthusiasts who are interested in sampling the local seafood or award-winning Westport Rivers winery. Kayak the Westport River or have food and drinks on the dock at The Back Eddy as you watch the sunset. Please note that we cannot provide sheets or towels at this time as we don't have a washer/dryer. You will need to bring your own.

Peaceful hideaway on Westport Point

Westport, Massachusetts, United States

3

Bed

Bath

5

Sleeps

$502.65

$3,500/weekbr1,450 sq ftbrbr1 bedroom penthouse (third floor) condo with 2 decks overlooking the Atlantic Ocean and Westport Harbor, Ma.brbrEvery room has ocean/harbour views, plus eat in Kitchen, laundry room, spacious living room with multiple closets.brbrRental includes outdoor grille and furniture, umbrellas, coolers, and completely furnished condo, etc.brbrAccess to semi private beach and wharf only steps away.brbr----------------------------------------------------------------------------------brALSO AVAILABLE OFF-SEASON!br$ 2,500/mobrSeptember 2023 - May 2024br*3-month minimumbrbrFirst, last, & security deposit required.brbrIncluded: basic wifi/streaming services, garbage pick up, water, off street parking.brbrNot included: electric and heatbr

Condo

1 bedroom penthouse, 3rd floor condo overlooking Ocean & Westport Harbor, MA.

Westport, Massachusetts, United States

Bed

Bath

6

Sleeps

$262.5

Guest cottage on 300-yr old historic farmstead, now a working goat farm. 360 sq ft open floor plan with Queen bed, decorative FP, loveseat pull-out, ++ seating, bistro table/chairs, WiFi, Roku TV, a/c & heat, 3 cu. ft. frig, m'wave, Keurig + Nespresso coffee makers/tea kettle. NO KITCHEN facilities. Full bath (shower stall). Bright & cheery, close to barn & goat pen but far enough from main house for privacy. Shaded grass patio w/ teak furniture and clothesline. Orchard (w/ fire pit), pastures, hay fields, stream, walking trails in woods.

Charming cottage on goat farm in picturesque Westport

Westport, Massachusetts, United States

Bed

Bath

Sleeps

$222.31

Located at the historic Head of the Westport River this luxurious stay is steps away from the Country Store for treats and treasures, the Watershed Headquarters with interactive displays and Osprey Kayak next door to experience the river for yourself. br It is an easy stroll to Mill Pond Conservation area to enjoy a rambling waterfall. brJust 6 minutes to the Central Village 14 min to Horseneck Beach, same distance to the Harbor.brThe Space:brThe beautifully renovated historic home offers exceptional private space for your vacation stay. Enter this federal style home to a mid century art gallery. The open sunny living and dining room boasts a mix of Cape and local art accenting a creative mix of contemporary and period furnishings.brThere are no kirchen facilities but your stay is enhanced by offering a micro, toaster oven, refrigerator with water and a beverage station with filtered water, coffee and teas.brNewly renovated first floor bath features a fully tiled walk in rain shower, heated floors and towel bar. What's better than wrapping yourself in a warm towel while prepping for the day or event with a light-up fog-free mirror! brYou will rest soundly in the 2nd-floor bedroom with a king-size Tempurpedic bed outfitted with fresh laundered and pressed linen sheets, soft cotton quilt and blanket. A cozy chenille chair for a restful reading spot.brbrSo many people are giving such great reviews of breakfast and I enjoy brightening the morning! When we are here and can offer this free service, we message our guests to let them know when a tray will be put out and ask about allergies.brbrGuest accessbrThis is a small historic river village located in a country setting. Summer parking is on the street with plenty of space available or an alternative can be provided.brOther things to notebrAdventurous walks and hiking abound in Westport. We can provide a conservation area trail guide and map of the best locations for beach access and area amenities.

Uncover rich American history and coastal charm when you stay with us!

Westport, Massachusetts, United States

Bed

Bath

Sleeps

$348.14

Land + Sea is an 1890s farmhouse in the Head of Westport neighborhood, just a few minutes walk to the East Branch of the Westport River. Spend the days kayaking nearby or at nearby beaches, then come back to rinse off in the outdoor shower. Close to Buzzard Bay Brewing, Westport Rivers Winery, farm stands, dairies, cycling loops, galleries/studios and conservation areas. Prepare local foods in the chef's kitchen or on the grill.

Country House

A country coastal retreat

Westport, Massachusetts, United States

Bed

Bath

Sleeps

$345.48

Looking for a quiet place to finish that book, write that song, explore seaside walks, or just get away from it all Come to our cottage in the charming hamlet of Westport. The cottage is a short walk from the Allen's Pond trail, Westport Town Beach, the Bayside Restaurant, and Gooseberry Island. A newly updated kitchen and interior provide a relaxing place to rest between adventures. There are two bedrooms: one with a queen-sized bed and another with a bunk bed (twin over a full with a twin trundle) that can sleep 4 people. The backyard abuts farmland and has a new patio, outdoor shower, and observation deck on the roof for ocean views.

Cozy Artist's Cottage by the Sea

Westport, Massachusetts, United States

Bed

Bath

Sleeps

$566.48

Enjoy summer in Westport, MA. Walking distance to Westport's East Beach. 2 bedroom,2 baths. Charming interior, large dining area, fully equipped galley kitchen. Bedroom and washer, dryer on the first level. Large master, bonus room with deck and Day bed on second floor. AC. Outdoor shower. Large deck. Explore the Westport Winery, Walk the Audubon Trail, and enjoy the Buzzards Bay Brewery. Beach chairs,towels,grill,everything you need.

Westport, Ma East Beach location.

Westport, Massachusetts, United States

Bed

Bath

Sleeps

$406

Located in bucolic coastal Westport, Massachusetts, this cottage is a peaceful retreat for guests seeking a relaxing getaway; perfect for unwinding after a day at the beach or sightseeing in nearby historic waterfronts. Situated amidst state conservation land, on a private lane, you’re walking distance to the beaches and nearby hiking and restaurants; minutes away from boating, kayaking and fishing access. Just a short drive or bike ride to nearby farm stands, winery, and local breweries.brThe cozy living room features a sleeping area with a king bed, living area features pullout sofa bed and two futon ottomans; comfortably accommodating sleeping for 4.With one fully equipped bathroom, guests will find everything they need for a comfortable stay. The kitchen/dining area furnished with stove, fridge, microwave and Keurig, is stocked with the basics for your convenience. brHeating and AC keep the space soothing no matter the season. Whether you’re curling up with a book or enjoying quiet moments on the spacious deck, this cottage offers an enjoyable escape. Enjoy all that Coastal Massachusetts has to offer when you stay at our charming respite.

Courtney's Cottage set in peaceful Westport cozy retreat for a relaxing getaway

Westport, Massachusetts, United States

Bath

Sleeps

$1484.3

Welcome to your perfect coastal escape on the East Branch of the Westport River in beautiful Westport, Massachusetts. This amazing waterfront cottage offers the ideal mix of relaxation, adventure, and classic New England charm.brbrInside, the home features a bright, open floor plan that brings everyone together. The spacious kitchen flows seamlessly into the dining and living areas, creating an inviting space for gathering, cooking, and relaxing after a day on the water. Large windows fill the home with natural light and frame peaceful river views.brbrWith 5 comfortable bedrooms, there’s plenty of space for family and friends. For larger groups, the third floor offers optional additional sleeping space,, giving you extra flexibility and a fun, tucked-away retreat feel—perfect for kids, teens, or additional guests.brbrStep outside and enjoy everything that makes this property special. Launch one of the provided kayaks directly from your private dock and explore the calm waters of the East Branch. After a day on the river or nearby beaches, rinse off in the outdoor shower and unwind while soaking in the waterfront setting.brbrYou’re just 5 minutes from the beautiful state beaches along Horseneck, the charm of historic Westport Point, dining at The Back Eddy, and convenient local groceries—making it easy to balance peaceful riverfront living with classic coastal New England experiences.brbrWhether you're kayaking at sunrise, enjoying beach days, or gathering together in the open living space at sunset, this Westport cottage is the perfect place to create lasting memories.

Waterfront Westport Retreat Dock-Outdoor Shower- 5BR + Bonus Loft- Near Beaches

Westport, Massachusetts, United States

Bed

Bath

Sleeps

$418.08

A lovely and relaxing private backyard, just a short walk/bike to Westport Harbor, beautiful Horseneck and Cherry & Webb beaches, and the Westport River. Professionally decorated with a rustic beach house vibe and comforts of home. Sleeps 6 comfortably. Large yard with sun and shade. Nearby restaurants including Westport Rivers Vineyard & Buzzard's Bay Brewery beckon after a breezy beach day. Plenty of farm-to-table and family friendly activities even on rest-from-surf days-- this is the place to be!brbrTake a brisk morning walk to Westport Harbor, passing stone walls and historic properties such as Captains' houses along the way. Or make an afternoon of slurping oysters and sipping Farmer's Fizz on the deck at Westport Sea Farms, a short stretch down the road. Rent a kayak and discover the Westport River, paddling to your heart's content.brbrUpon your return, relax on the stone patio in Adirondack chairs while enjoying ocean breezes, or choose a shady spot in the green backyard.brbrBring your bikes! A newly built, paved bicycle/walking lane begins a block away from your front door and leads you over the bridge to Horseneck Beach or Cherry & Webb beach, 2 miles away .brbrDrive to Westport Village center for shopping, dining, and groceries, only 8 minutes away. Browse the Saturday Farmer's Market where you will find grass-fed local beef, local honey, organic cotton hand-made sheets, and tomatoes to die for. Or drive around to the many farm stands along the winding town roads.brbrSleeping arrangements (sleeps 6 comfortably):br• 1st fl. bedroom: 1 king bedbr• 2nd fl. larger bedroom: 1 queen bed br• 2nd fl. smaller bedroom: 2 twin bedsbr• 1st floor living room: sleeper sofa, sleeps 2.brbrAmenities include:br✓ Washer and dryerbr✓ All linens and towels will be provided.br✓ Well-stocked kitchen with all the cookware, dinnerware, silverware and utensils you may need.br✓ Wireless internetbr✓ Gas stove and ovenbr✓ Microwavebr✓ Full-size refrigeratorbr✓ Backyard gas grillbr✓ Window air conditioners in each bedroombr✓ Driveway parking for 3 carsbr✓ Parlor games and booksbrbrCheck-in at 4pm; Check-out at 10am. Summer bookings are 7 nights, Sat-Sat.brbrGuests will have access to the entire house, inside and out including the attached porches, patio, and a private backyard.

☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village

Westport, Massachusetts, United States

Bed

Bath

Sleeps

$283.24

Located on the east branch of the Westport River this 1790-built Georgian house is a fine place for your vacation. Seven miles from beautiful Horseneck Beach, set in the heart of the historic “Head of Westport” neighborhood, this lovingly restored three-bedroom home captures a time gone by.brbrWith a fully equipped kitchen and spacious dining room, delicious meals can be enjoyed at a table for 6. The master bedroom has a queen bed, while the 2 upstairs bedrooms have full-size. All the bedrooms have A/C, but every afternoon around 4 or 5 the cooling breeze comes up the river, and makes the sitting on the patio a treat.brbrFind a quiet spot in the garden to read, or sit on the back yard patio in the morning enjoying coffee and birdsong.brbrThere is a seafood market down the road where the freshest fish and shellfish can be bought to put on the gas grill. One can eat nothing but local fruits and vegetables from farm stands and farmers’ markets (when in season).brbrKayaks and paddleboards can be rented across the road. Or you can bring your own to put in at the town landing there. The Head is an ideal place to start a bike ride. Westport has great roads and (mostly) polite drivers.brbrA short walk brings you to a country store featuring ice cream and penny candy and fresh made donuts. brThe rolling hills of farmland and salt water rivers are unique to New England.br

Historic Village Setting

Westport, Massachusetts, United States

Bed

Bath

Sleeps

$437.23

Relax on the deck of this private, roomy beach getaway with AC! Listen to the sounds of the ocean and birds. The huge open concept livingroom/diningroom has cathedral ceilings, a ceiling fan and is great for family dinners and entertaining. The granite kitchen is open to the livingroom and the 3 bedrooms are all bright and clean. The two bathrooms have new floors, fixtures and lighting.. The master bedroom has an attached full bathroom with a new w/d. The wall of windows look out onto the deck with gas grill, and also look out to a huge backyard and a stone wall. An outdoor shower is great for after a sandy beach day. Walking 5 minutes down the private road you get to a picturesque bay with kayaks and sailboats. Lovely family neighborhood. A kayak is available to take serene rides on the Westport river just steps away. A 5 minute ride to spectacular ocean beaches. Nature preserves, great restaurants, horseback riding and movies, museums, malls, and minigolf are all a 10-20 minute ride away. brHouse has one queen bed in master bedroom. Other bedrooms have full beds. Linens and towels provided.brbrBefore booking is accepted, traveler must sign the rental agreement and upload to VRBObrbrbrbrbr brbrKeywords: Quiet, private, sunny, relaxing, ranch,

Relaxing , Spacious Westport Retreat

Westport, Massachusetts, United States

3

Bed

Bath

6

Sleeps

$437.17

6 Mi to the Beach | Spacious Interior for Groups | Ample Outdoor Lounge SpacebrbrWhether you're in town for university tours or getting your new student settled in, you'll discover the perfect base for exploring Massachusetts and Rhode Island spots alike at this Westport vacation rental. After day trips and adventures, evenings at home bring you together for barbecue dinners on the deck and starlit chats by the fire. Local charm and coastal fun are all within reach — secure your dates today!brbr-- THE PROPERTY --brbrROC-20523108-003 | C0572823340brbrINDOOR LIVINGbr- Smart TVs, dining tablebr- Basement lounge w/ TV, darts, board gamesbr- Portable A/C units, washer & dryerbrbrOUTDOOR LIVINGbr- 2 decks, water viewbr- Outdoor lounge seating, dining setbr- Paved patio w/ fire pit, gas grillbr- There is NO public water access from this propertybrbrKITCHENbr- Dishwasher, refrigerator, stove/oven, microwavebr- Keurigbr- Cooking basics, dishware & flatwarebrbrACCESSIBILITYbr- Multi-level home, stairs to enterbr- All bedrooms on upper levelbrbrPARKINGbr- Carport (1 vehicle)br- Driveway (1 vehicle)brbr-- THE LOCATION --brbr- 19 miles to Newportbr- 48 miles to Gillette Stadiumbr- 10 miles to Roger Williams Universitybr- 24 miles to Brown Universitybr- 28 miles to Providence Collegebr- 25 miles to Johnson & Wales University Providencebr- 22 miles to Salve Regina Universitybr- 8 miles to University of Massachusetts Dartmouthbr- 10 milesto Bristol Community Collegebr- 30 miles to Bridgewater State Universitybr- 6 miles to Grinnell's Beach, 9 miles to Island Park Beachbrbr-- 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- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This multi-level home requires stairs to enter; all bedrooms are on the upper levelbrbrSECURITY CAMERA INFORMATIONbr- 2 exterior devicesbr- Location: front entrance, front of the house, carportbr- Coverage: entrance, front of the house, parking

New England Cottage! Water Views & Decks

Westport, Massachusetts, United States

Bed

Bath

Sleeps

$1957.94

This spacious three level family vacation home offers sweeping views of Richmond Pond and the Atlantic Ocean, and you will enjoy especially great sunsets. Easy walking distance (appx 600 yards) to residents' beach. Additional access to Elephant Rock Beach Club available for additional fee. (ERBC Rules apply.)brAir conditioning on all levels; WIFI; sleeps 11, including 2 en suite master bedrooms each with a king bed; washer/dryer; two dens on different floors, each with a TV; large yard on quiet private road; deck with grill; stone patio with lounge chairs and sofa/chairs; outdoor shower; ping pong table.

5 bedroom ocean and pond view home in Westport Harbor

Westport, Massachusetts, United States

5

Bed

Bath

11

Sleeps

$502.65

Welcome to this charming house in Westport Harbor, near River and Ocean beaches. This vacation rental is the perfect home away from home for guests seeking a cozy, comfortable stay. With 4 bedrooms, including 2 full beds and 2 twin beds, there's plenty of space for everyone to unwind and relax. Private setting surrounded by open fields, gardens. Whether you're exploring the local attractions or simply enjoying the gorgeous surroundings, this comfortable house is the ideal base for your adventures. Experience the natural beauty of Westport and nearby Little Compton,RI at our house.

Charming Westport Harbor Cape

Westport, Massachusetts, United States

Bed