Guest house holiday rentals in Edgartown

Guest house in Centerville

A charming carriage house with shingle siding is set against a blue sky adorned with fluffy clouds. A black Jeep is parked in front, showcasing the gravel driveway. Lush greenery surrounds the property, enhancing its inviting appearance.

5 out of 5 average rating, 146 reviews

Modern Fireplaced Carriage House with Beach Permit

Feel at home & relax in our new one bedroom carriage house. Modern yet classic Cape Cod style and elegance. Rest easy on a new Stearns & Foster king size mattress with designer linens and furnishings. Cozy up to the fireplace and flat screen TV. Custom bathroom, Bosch laundry units and small deck. Kitchenette with dishwasher drawer, under cabinet refrigeration, microwave, toaster, Keurig coffee maker, Starbucks coffee and various teas. We offer beach chairs, bags & towels for your convenience.

4.98 out of 5 average rating, 230 reviews

A bright sleeping area features a spacious white bed with decorative pillows and bedside lamps. A small kitchen area with light-colored cabinetry is visible in the background, complemented by a large window allowing natural light. A cozy seating area adds to the warmth of the space.

Guest house in Chilmark

Beautiful Guest House in Chilmark

This newly renovated guest house is located in a quiet and very private setting in Chilmark. The guest house is located above the garage adjacent to the main house with a private entrance. It has a queen size bed with two oversized chairs. There is a full bathroom and outdoor shower. A small kitchen features butcher block countertops, stainless steel sink, refrigerator and 2 burner electric stove and island. Air conditioning and heat. The space comes with a walk -on-pass to Lucy Vincent Beach.

Guest house in Woods Hole

A quaint cottage exterior is surrounded by lush greenery and vibrant flower beds. The building features a shingled façade, a prominent chimney, and multiple windows, providing a welcoming appearance. A pathway leads to the front door, framed by colorful plants, enhancing the inviting ambiance.

4.89 out of 5 average rating, 195 reviews

Quaint Cape Cod Cottage

Quaint cottage on Cape Cod, perfect for a last minute getaway. Amazing location with the beach, Shining Sea Bike Path, The Knob, and Spohr Gardens all within WALKING DISTANCE! A five minute drive to Falmouth Main Street which offers amazing restaurants and shops. In the other direction, another five minute drive will bring you to the historical seaside village of Woods Hole, home to world renowned scientists, numerous beaches, restaurants, museums, an aquarium and the Martha's Vineyard Ferry.

A bright living area features a comfortable seating arrangement with soft, neutral-toned couches. Natural light fills the space through multiple windows, and a rustic wooden coffee table enhances the cozy feel. A small dining area is visible in the background.

5 out of 5 average rating, 25 reviews

THE BIG CHILL ~ ONE MILE TO EDGARTOWN CENTER

The Big Chill is close to the buses, grocery stores, fish markets, Morning Glory Farm, the beautiful beaches and the center of Edgartown. You’ll love it.. its cozy, has A/C, you'll love the high ceilings on the second floor and the location! The BIG CHILL has a full bath indoors and a fully enclosed outdoor shower steps from the door. Great for couples, solo adventurers, and business travelers….a bike ride to town. If you need a bigger house, check out Sandy Feet Retreat for 5-10 guests.

An open studio layout is showcased, featuring a spacious bed with a metal frame. A cozy seating area is arranged with patterned cushions and a wooden coffee table. Natural light pours in through multiple windows, illuminating the warm wood flooring and inviting ambiance.

4.97 out of 5 average rating, 92 reviews

Vineyard Meadow Artist Studio

This lovely artist's studio is just steps from miles of trails. Walk to the beach or meander through the woods of Long Point Wildlife Refuge, experiencing the serenity of this still untouched corner of Martha's Vineyard. This studio includes a bathroom with a shower, a washer/dryer and a kitchenette. It is the perfect spot for a lone artist, a couple or a family to enjoy Martha's Vineyard any time of year. This property shares the driveway and parking with Vineyard Meadows Writer's Cottage.

A well-lit bedroom features a spacious bed with white linens and decorative pillows. Natural light enters through two windows adorned with blinds. A soft area rug is positioned under the bed, complementing a cozy reading nook with a rattan chair and a bean bag.

4.96 out of 5 average rating, 45 reviews

Wedding RetreatTrails Golfing Beaches Private Gem

✨ LOCATION, LOCATION✨ ✅Cleanliness, Fully stocked kitchen ✅Pet-Friendly, Minutes from ferry & beaches ✅ Peaceful & private neighborhood 🌳 Hidden trails—Great for exploring 🏡 Perfectly Getaway, ✅ Easy access to all towns, Hassle-free stay. 🚗 Just 8 minutes to local markets, and top-rated restaurants. 🚴‍♂️ A scenic 13-minute bike ride takes you to the charming Edgartown Village or Katama South Beach—perfect for breathtaking sunsets! Convenience, comfort, and nature at your doorstep.

4.99 out of 5 average rating, 106 reviews

The open living area features exposed wooden beams overhead and includes a spacious wooden dining table. Two lounge chairs, a round pouf, and a day bed are arranged for seating. Natural light filters in through large glass doors, leading to an outdoor area.

Guest house in Chilmark

4-Season Guest House on Historic Chilmark Estate

Beautiful private guest house in Chilmark on Martha's Vineyard. Secluded yet convenient. Drive on pass to spectacular Chilmark beaches! Newly renovated and gorgeous. Great location - 10 minute walk to Chilmark Store. Full kitchen, living area, kitchen island/dining table, queen bed, day bed (not for sleeping), fireplace/heater, private outdoor shower, deck and picnic table, full bath inside. Keurig machine. 2 friendly labs/2 chickens on premises. Easy bus access. Old-style MV charm.

Guest house in Vineyard Haven

4.95 out of 5 average rating, 136 reviews

West Chop Cottage + Beach Access

Sweet, rustic, and tiny - yet comfortable with all the amenities - the cottage is a short walk to the town center, lighthouse, landmarks, and lovely harbor beaches on desirable West Chop. The private yard with harbor view allows for sunbathing and stargazing, lounging and lawn games, grilling and campfires. With access to spectacular private association ocean beach, Hancock Beach, on the island's south shore in Chilmark, this rental offers a complete Vineyard experience.

The exterior of Salt Tide Cottage is shown, featuring a white-sided structure with a dark blue door and a large star decoration. A small seating area with two chairs and a table is positioned in front, surrounded by well-maintained green grass and trees.

4.88 out of 5 average rating, 151 reviews

Relaxing Cottage in Centerville Village

Welcome to my home! The cottage is located in Historic Centerville Village, it's a welcoming, bright and relaxing, studio space; perfect for a couple, or individual, to getaway on Cape Cod. Salt Tide Cottage is a private guesthouse with off-street parking and a serene outdoor space. It sits behind the main house with its own back yard space with hammock. Just a short walk to the ocean, beaches, the library and the general store.

Guest house in South Yarmouth

A shaded patio area is framed by a white pergola adorned with blooming wisteria. A wicker loveseat with floral cushions and a matching lounge chair are positioned along the paved surface, creating a relaxing outdoor space surrounded by greenery.

4.96 out of 5 average rating, 223 reviews

“The Pink Cottage” in Historic South Yarmouth

“The Pink Cottage” is a charming one-bedroom private building nestled into a beautiful historic property in South Yarmouth. Enter through the pergola patio, enjoy a spacious living space with dining and kitchen area. The one-bedroom with large closet is comfortably outfitted with all linen necessities, full bath with stand-up shower. Outdoor shower just off the patio, grill and more! Very quiet and private.

Guest house in Vineyard Haven

A charming cottage is surrounded by lush greenery and blooming hydrangeas. A small Weber grill is positioned on the stone patio, and a wooden pathway leads to the covered porch. The facade features multiple screened doors and windows, inviting natural light into the space.

4.85 out of 5 average rating, 275 reviews

Sweet Vineyard Haven Cottage

Booking for Fall 2025 is still OPEN. BOOKING for 2026 season to OPEN Oct. 15th Walk to Main Street Vineyard Haven and ferry from this classic, comfy cottage with great screened porch and well equipped kitchen. No car, no problem. Upgraded A/C, premium cable and a new outdoor shower!

Guest house in Dennis Port

The exterior of a charming cottage displays a sloped roof with shingles and large windows, framed by lush greenery. An American flag is proudly displayed above the entrance, while colorful flowers and plants enhance the area in front of the house.

4.86 out of 5 average rating, 285 reviews

Joe's Beach Hideaway

Beach is at the end of the dead end road! Very Cute romantic cape cottage! Inside: Queen bed, dresser, couch, new kitchen and bath Outside: table and chairs, outdoor shower, beach chairs, umbrella and grill House has wifi, cable and parking for one car!

Popular amenities for guest house rentals in Edgartown

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

The open-concept living area features a modern kitchen with stainless steel appliances and white cabinetry. Bar seating is provided at the kitchen's high-top counter, while a glass coffee table centers the space. A door leads to the outdoor area, enhancing natural light.

Guest house in West Dennis

*NEW* Cape Cod Bungalow

A cozy living area features a comfortable sofa with neutral-toned upholstery, accompanied by a decorative throw pillow. A wooden dining table with chairs is situated nearby, complemented by warm lighting from a pendant fixture. Natural light enters through two small windows.

Cozy Apartment Nearby Pond, Beaches, Golf Course.

A cozy bedroom features a spacious bed dressed in light bedding. A bedside table holds a lamp, while greenery adorns both ends of the bed. Two windows allow natural light to fill the room, framed by light curtains that complement the inviting decor.

4.95 out of 5 average rating, 21 reviews

Sweet Millie Guesthouse

Superhost

Guest house in Dennis

New place to stay

“My Two Buoys” (Side B) Sleeps 6 / Walk to Beaches

A comfortable living area features a blue upholstered sofa and a stylish accent chair. Natural light enters through the two windows with wood blinds. A dining table is visible in the background, providing additional seating options, while a decorative area rug adds warmth to the space.

Private room in South Yarmouth

Carriage House Retreat in the Heart of Hyannis!

4.46 out of 5 average rating, 13 reviews

Yarmouth summer rental vacation

4.92 out of 5 average rating, 13 reviews

A bright living area features a light-colored sofa adorned with soft throw pillows, facing a round coffee table. Large double doors open to a private outdoor space, where a cozy seating area is visible. Natural light illuminates the room, enhancing the airy atmosphere.

Guest house in Nantucket

Beach Chic Guest Cottage, Town

4.93 out of 5 average rating, 85 reviews

The exterior of the cottage is shown, featuring light brown shingles adorned with climbing greenery. The well-maintained lawn is bordered by flowerbeds. A white wooden gate leads to the entrance, which is framed by large glass doors. Morning sunlight illuminates the serene setting.

Guest house in Nantucket

Ideally located in Town, 2 blocks from water

Guest house rentals with a patio

A patio dining area is set with a glass table and four wicker chairs. A bottle of wine stands at the center, accompanied by two glasses and two plates. Surrounding greenery creates a natural backdrop, enhancing the serene outdoor dining experience.

4.92 out of 5 average rating, 26 reviews

Private cabin in Wildlife Habitat; near bus route

A private deck is framed by lush greenery, featuring two wicker chairs and a small table. The entrance is marked by glass doors that open to the cottage, with light filtering through the surrounding foliage.

4.98 out of 5 average rating, 41 reviews

Private Two bedroom Katama cottage near Edgartown

Guest house in West Yarmouth

The exterior of a charming duplex features a pathway lined with colorful shrubs and plants. A welcoming front porch leads to light-colored siding, with a blue door providing a pop of color. Adjacent to the entrance, a wooden trellis adds character to the outdoor space.

5 out of 5 average rating, 53 reviews

Cozy, renovated home in a charming duplex cottage

A rustic studio cottage is presented with a sloped roof and blue siding. A wooden deck leads to the entrance, flanked by a garden with flower beds. A grill is visible on the deck, and a stone pathway meanders through the green yard.

5 out of 5 average rating, 37 reviews

Charming W. Tisbury Studio Guest Cottage

4.9 out of 5 average rating, 39 reviews

The exterior of a cottage is presented, featuring textured wooden siding in muted gray tones. Multiple windows allow natural light to enter, and a white front door adds contrast. A stone pathway leads to the entrance, surrounded by an open grassy area.

Guest house in Nantucket

Conveniently-located cottage with on-site parking

Guest house in West Hyannis Port

A cozy interior features wooden walls and a sloped ceiling. A striped couch is positioned near a wooden coffee table, while a cushioned armchair adds to the seating options. Natural light enters through the glass door, highlighting the inviting ambiance.

4.9 out of 5 average rating, 20 reviews

Beach glamping at the Zen Den

Guest house in South Yarmouth

An open kitchen and dining area is visible, featuring a round table surrounded by four chairs. A well-equipped kitchen includes a stove, refrigerator, and ample counter space. Light gray walls and bright lighting create a welcoming atmosphere in this cozy cottage space.

5 out of 5 average rating, 36 reviews

Cozy Cottage

Guest house in Oak Bluffs

A stone patio features a round dining table surrounded by chairs, shaded by a vibrant red umbrella. A barbeque grill is visible nearby, with a backdrop of lush greenery and weathered wooden structures, creating a cozy outdoor space.

4.95 out of 5 average rating, 20 reviews

Cozy Vineyard Cottage

Guest house rentals with a washing machine and dryer

The kitchen features modern cabinetry and a large quartz countertop. Stainless steel appliances, including a refrigerator and microwave, are prominently displayed. A sink is positioned near a window, while three bar stools are arranged along the countertop for casual dining.

5 out of 5 average rating, 3 reviews

New! Edgartown Guest House in a garden setting

Guest house in Oak Bluffs

A dining area is presented with a rustic wooden table, set for a meal. Four dark chairs surround the table, and a vase of white flowers adds a touch of decor. The adjacent living area features a comfortable sofa, flanked by windows allowing natural light.

4.99 out of 5 average rating, 98 reviews

Mermaid Cottage

A bright living room features high ceilings and large windows allowing natural light to fill the space. A gray sofa and matching armchair are arranged around a light blue coffee table. A flat-screen TV is positioned on a light wooden media console across from the seating area.

5 out of 5 average rating, 27 reviews

Guesthouse

A bright living area features a striped couch adorned with a 'SUMMER HOUSE' pillow, complemented by a cozy armchair. Natural light enters through windows with white blinds, and wooden beams add a touch of character. A decorative coffee table sits in the center, enhancing the inviting space.

4.9 out of 5 average rating, 70 reviews

Osterville Guest House

A calm bedroom features a spacious bed layered with floral bedding, complemented by wooden furniture. Light filters through two small windows and a glass door, while soft green curtains frame the entrance. A cozy ambiance is created by a bedside lamp against the warm yellow walls.

4.95 out of 5 average rating, 22 reviews

Guest house over Garage

A wooden gate opens to a lush garden, framed by tall greenery and vibrant flowers. A pathway made of stones leads through the garden, offering a welcoming entrance to the cottage. Sunlight highlights the natural beauty of the space on a clear day.

4.76 out of 5 average rating, 51 reviews

Marthas Vineyard 1BR Cottage 10 min to beach/town

5 out of 5 average rating, 23 reviews

The bungalow's exterior showcases a quaint two-story structure adorned with shingled siding. A balcony is visible on the second floor, decorated with patriotic accents. The ground level features a covered porch with seating and a barbecue grill, surrounded by lush greenery.

Guest house in Tisbury

Escape to Bungalow 24 on MV!

A cozy seating area is displayed with a white, weathered coffee table topped by a wooden tray, containing a book and candle. A glass vase holds purple irises, while a small potted plant adds greenery. Two artworks depicting flowers are hung on the wall behind a plush sofa.