Vacation rentals in Chappaquiddick

4.97 out of 5 average rating, 71 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

Charming and renovated cottage is a 5-minute bike ride to the Chappy ferry point & beach and a 10-15 minute walk to the Mary 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.

Guest suite in Oak Bluffs

A spacious living room is highlighted by a large grey sectional couch adorned with various throw pillows. A wooden coffee table sits in front, featuring storage compartments. Two abstract paintings in calming blues are displayed above the couch, while soft lighting illuminates the area.

4.95 out of 5 average rating, 381 reviews

Lovely 2 BR Oak Bluffs Apartment

This 100% private apartment is on the first floor of a shared house where owners and their son live upstairs. There are no shared spaces. You have a private entrance and parking. The living room, bedrooms, bathroom, and kitchenette are bright and clean. It is exactly 1 mile from Oak Bluffs Center, a half mile from The Cottages and Farm Neck Golf Course, and a block from Tradewinds walking trails. Across the street is the bike path, & the bus stop is on the corner for easy island transportation!

4.94 out of 5 average rating, 201 reviews

The exterior of a charming house is shown, featuring a gray shingle facade and a welcoming covered porch. Lush greenery and ornamental shrubs frame the entrance, while a gravel driveway leads up to the front door, creating an inviting approach.

Home in Oak Bluffs

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, ENDS 9/1) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

The exterior of a historic home is displayed, featuring a shingle-style facade and a white front door. Lush green lawns surround the house, complemented by neatly trimmed shrubs and flowering plants. A clear sky with scattered clouds creates a serene atmosphere.

5 out of 5 average rating, 14 reviews

Spacious Waterfront w Private Beach sleeps 10

This historic home with a private beach in Edgartown sleeps 6 in the main house and 4 in the guesthouse. Perfect for entertaining, enjoying family or reconnecting with friends. The main house has an open concept kitchen, dining room and living room with a large deck facing the water. Plenty of space to lay out and relax plus an enclosed porch for late night card games and drinks. The home is a leisurely 10 min walk into Edgartown for morning croissants at Rosewater and dinner at The Atlantic.

An open concept living space features a dining table surrounded by black chairs, with a view of the backyard through large glass doors. A cozy seating area with light-colored sofas is visible, complemented by a decorative wall and modern furnishings. Natural light enhances the warm ambiance.

4.98 out of 5 average rating, 65 reviews

Walk to Town/Golf Club - Renovated Edgartown Home

The perfect retreat for your escape to Martha's Vineyard, walking distance to downtown Edgartown! Location, location, location! We're a stone's throw from Edgartown Golf Club and all the amazing restaurants + shops are just a 10 minute stroll. This 2-bedroom, 2-bathroom home has been completely renovated, with an all-new kitchen, bathrooms, furnishings, linens & accessories. The house accommodates 5 people very comfortably, and is located on a quiet residential street just off Upper Main.

4.98 out of 5 average rating, 218 reviews

An open studio space features a cozy sleeping area with a spacious bed covered in light bedding. A soft armchair and a wooden bench provide additional seating. Natural light streams in from a window, enhancing the room's bright atmosphere. Shelving displays books and decorative items.

Apartment in Oak Bluffs

Sunny Studio Apartment on Martha's Vineyard

Our Sunny Studio is centrally located on Martha's Vineyard. A down-island location with an up-island feel. Open and airy studio with kitchenette and bath. The apartment has all the essentials. The apartment is located within walking distance of hiking and biking trails. A 10 to 15 minute car ride to any down-island town / beach. ***Please Note: Although conveniently located we are not within walking distance to Bars or Restaurants. We do recommend first time visitors rent or bring a car.

The exterior of a newly constructed guest house is shown, featuring a spacious deck with seating arrangements. Surrounding plant beds with fresh landscaping complement the wooden structure, while a gravel pathway leads towards the entrance, creating an inviting outdoor space.

4.96 out of 5 average rating, 247 reviews

Brand new gorgeous 2 bedroom guest house.

This is a gorgeous brand new 2 bedroom guest house on the bike path that leads to downtown Edgartown and both State Beach and South Beach, as well as 1/4 of a mile from the famous Morning Glory Farm Stand. There are cathedral ceilings in the living room, which provide a open, spacious feel. There is a large deck on the front of the house with a grill, table and chairs. Part of it is covered in shade. Separate parking for guests with privacy, as it sits 200+ feet from the main house.

Superhost

A charming cottage exterior is presented with dark wood shingles and white trim. A covered porch with seating overlooks a lush garden and landscaped area. French doors open to the outdoors, and a balcony is visible above, enhancing the inviting approach to the home.

4.91 out of 5 average rating, 100 reviews

Edgartown Trumpet Vine: Walk to Everything

You will feel right at home in this owner/architect designed 2-bedroom, 1 ½-bath house with original art in the heart of Edgartown, nestled in a garden oasis. Located between Cooke and Main St, this home is a short walk to everything a charming small town has to offer including great restaurants, Main St. shopping, a movie theater and the scenic harbor. The home provides an ideal base to explore Martha’s Vineyard for a romantic couples getaway or a family vacation with young kids.

4.98 out of 5 average rating, 344 reviews

A cozy outdoor seating area is arranged with several white lounge chairs on a gravel surface. A brick fireplace is positioned near the house, accompanied by potted plants and a view of the deck area adorned with covered furniture in the background.

Cottage in Tisbury

Martha's Vineyard Getaway Cottage

Contemporary cottage on quiet, private, wooded lot. Pristine, bright & comfortably furnished. Open living area, hardwood floors, vaulted ceilings, indoor/outdoor fireplaces, well appointed kitchen, washer/dryer, cable/internet/phone with unlimited national calling, SmartTV with Netflix and additional internet streaming services. Walk or bike to beaches and trails, 5 minute drive from downtown shops and restaurants. Property abuts West Chop Woods with lovely, quiet walking trails.

4.92 out of 5 average rating, 273 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

Unique Luxury Yurt w/ Free kayaking

Step into this unique yurt house! As soon as you walk in, you'll be greeted with a one-of-a-kind experience, from the textured concrete floors to the large circular skylight. Every detail is carefully planned, and you'll have the opportunity to unwind in a spacious private yard. Spend your evenings stargazing, take advantage of complimentary paddling, participate in our scheduled chicken feedings, do yoga in the roomy loft, and revel in the splendor of your exclusive island yurt!

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.

4.99 out of 5 average rating, 187 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.

The entrance of a condo is framed by a well-maintained lawn, with vibrant greenery and colorful flowers surrounding the doorway. The front door, featuring a decorative glass panel, opens to a sunlit pathway lined with stone pavers.