Holiday houses in Chappaquiddick

5 out of 5 average rating, 37 reviews

Home in Mashpee

Ocean View Cape Cod Beach Cottage

Experience a truly one-of-a-kind Cape Cod getaway in this classic beach cottage, tucked in New Seabury, Mashpee. Just steps from a private beach and a short stroll to Popponesset Marketplace, it captures the essence of coastal charm. Ocean breezes, golden sunsets, BBQs, and an outdoor shower make it the quintessential summer retreat. Popponesset Marketplace (10min walk) is closed during the off season but Mashpee Commons (10min drive) is open Saturday - Saturday rentals only during July/August

FamilyLocationBarbecue

4.96 out of 5 average rating, 24 reviews

Walk to downtown Edgartown in a quiet neighborhood

This house is on a peaceful side street just a 15-min walk to Edgartown Village. It has 3 bedrooms, 1 bath, a well-equipped kitchen, a porch, and a grill for summer cooking! This space is a second-floor unit; the first floor is occupied by the owner. Both units are completely separate with private entrances and no shared spaces. Close to multiple popular beaches, the town library and playground, and just around the corner from the island's largest grocery store make this a great home base!

LocationFamilyComfort

4.97 out of 5 average rating, 76 reviews

A charming cottage features a shingle exterior surrounded by lush greenery. Large windows invite natural light, and a welcoming entryway is accentuated by steps leading to the front door. The tranquil wooded setting enhances the peaceful atmosphere of the property.

Cottage in Edgartown

Chappy cottage close to ferry & walk to beach

Booking for '26 Season. Charming cottage is a 5-minute bike ride to the Chappy ferry & beach and a 10-15 minute walk to the Frances Preserve beach. Located in a quiet wooded setting, the property offers new furniture and beds; renovated kitchen with dishwasher and microwave; new bath w/ shower/tub; washer/dryer; hardwood; screen porch; deck & outdoor shower. Cable, wifi (200 megs), AC, ceiling fan, grill, deck furniture, beach chairs & umbrella. The rental season runs mid May through late Oct.

LocationFamilyOutdoor spaces

5 out of 5 average rating, 125 reviews

A private garden patio is showcased, featuring a circular table surrounded by four chairs. Plush cushions in vibrant blue patterns adorn the seating. Nearby, two wooden lounge chairs offer additional relaxation options. Lush greenery and flowers provide a natural backdrop, enhancing the outdoor ambiance.

Apartment in Edgartown

Outdoor Shower, Private Garden Patio, Walk to town

* Private garden patio: string lights create chill evenings around the propane fire pit. Table & chairs, propane grill, & enclosed outdoor shower * 10 min walk to Edgartown's dining & boutiques * Cable TV, Streaming services, Sonos * High-speed WiFi, comfortable workspace in the bedroom * USB charging ports in the BR & LR * Small but mighty fully stocked kitchen for home-cooked meals * Organic, local bath products * Board games & a small library * HW floors, SS Bosch appliances, DW, W/D, HVAC

FamilyValueCondition

5 out of 5 average rating, 20 reviews

Home in Sandwich

The Gilded Anchor

Located in East Sandwich, Cape Cod, the property offers a blend of coastal beauty and natural tranquility. Directly across the street from the bay, you’ll enjoy immediate access to the beach and expansive marshlands steps from the back deck. The updated interior and modern comforts of this two-bedroom home includes a bonus loft space along with a spacious living room and dining room that open up to the expansive back deck with tidal views. Easy access to local shops, cafes, and restaurants.

LocationFamilyOutdoor spaces

4.91 out of 5 average rating, 104 reviews

The interior features a wooden wall with a triangular peak highlighted by a small window, allowing natural light to filter through. A pendant light hangs from the ceiling, complementing the rustic aesthetics of the space.

Guesthouse in Edgartown

Martha’s Vineyard Cottage - A Glamping Experience!

This is your vineyard home, where you can walk or ride a bike less than a mile to the beach or two into town. Get the glamping experience with kitchenette, A/C, an outdoor shower, a composting toilet, a queen bed in the loft and futon couch that can sleep two more in the living room. Enjoy outdoor games, outdoor seating, a Weber grill for bbq, tv, WiFi, cozy indoor space and more, right on the bike path with a bus stop for easy accessibility or free car parking. Whatever you want!

FamilyLocationQuiet

A charming two-story cottage features a shingled exterior with a pitched roof. The inviting front porch is supported by wooden pillars and surrounded by lush greenery. A white picket fence encloses the well-kept lawn, creating a warm curbside appeal.

5 out of 5 average rating, 24 reviews

Martha's Vineyard Cottage: Walk to Town and Beach

Updated 1920s Cottage in Edgartown Village – Walk to Beach, Harbor and Main Street Step into classic Vineyard charm at this fully updated 4-bed, 3-bath craftsman cottage in the heart of Edgartown. Two blocks from Main Street’s restaurants, galleries, and harbor and a quick walk to Fuller St Beach & Lighthouse Beach. Fully winterized + AC, high-speed Wi-Fi, three workstations. Ideal for families, bachelorette parties or anyone craving a New England coastal escape.

FamilyLocationOutdoor spaces

4.92 out of 5 average rating, 305 reviews

The exterior of the yurt showcases a circular wooden structure with large, rounded windows, complemented by a metal roof. A private yard features lush greenery, colorful flora, and outdoor seating arrangements, creating an inviting space for relaxation and outdoor activities.

Home in Oak Bluffs

The Luxury Vineyard Yurt

Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

LocationValueAir conditioning

5 out of 5 average rating, 12 reviews

A bright living space features white walls and a wooden ceiling with ample natural light. A round coffee table is centered in the room, surrounded by a sofa and wicker chairs. A side table holds a lamp, and a colorful artwork is displayed on the wall, with ocean views visible through windows.

Cottage in Edgartown

Beachfront Cottage w. Yard + Town Access

Welcome to The Mizzen Cottage! Updated 1930's cottage on an ocean front compound on beautiful Chappaquiddick. Complete with a picturesque porch overlooking the outer harbor, side deck, outdoor shower, washer/dryer, dishwasher. Stunning views of the Edgartown lighthouse and Cape Poge. Access to a private beach. Access town with just a 10 minute walk (or 1 minute drive) to the Chappaquiddick Ferry, and be in downtown Edgartown in 15 minutes or less!

LocationFamilyGetting around

Guest suite in Oak Bluffs

A well-appointed efficiency suite features a spacious bed with soft linens against a light-colored wall. Two comfortable chairs and a small table are positioned near the bed, creating a quaint sitting area. Natural light enters through several windows, enhancing the inviting ambiance.

4.98 out of 5 average rating, 195 reviews

Quiet Hide Away

Lovely efficiency suite with private entrance in a quiet neighborhood. Private space located over attached garage. Plenty of space for two guests. Comfortably appointed with queen bed, dining set, living area with tv and full bath. Enjoy a coffee or cocktail on the private deck. Toaster oven, refrigerator and coffee maker will start your day right before heading to nearby beaches, golf courses or shopping.

LocationValueBeach

A welcoming entrance is framed by a neat sidewalk leading to a white front door, flanked by two windows. The exterior showcases classic shingle siding, with vibrant flowering shrubs and a well-maintained lawn adding charm to the inviting facade.

4.97 out of 5 average rating, 199 reviews

20-minute walk to Edgartown Village!

This 1550 square foot Ranch-style Condo with loft was built in 2018 and is set on a large nicely landscaped lot with plenty of room inside and out. It has It has 3 bedrooms and sleeps 8. It’s a 20-minute walk to the Edgartown village center, a 10-minute walk to Morning Glory Farm, and just a 10-minute drive to South Beach! All updated furnishings, beds, linens, appliances. Read our reviews! Immaculate!

LocationValueDecor

A light-filled living room is showcased with a comfortable sofa, side chairs, and a flat-screen TV. A brick fireplace is centered in the room, adorned with a round mirror and decorative items. Natural light filters through the windows, enhancing the inviting space.