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Martha's Vineyard, MA vacation rentals
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Best Vacation rentals and Airbnb offers in Martha's Vineyard, MA

Best family friendly Martha's Vineyard, MA vacation rentals

Among the 1635 accommodations in Martha's Vineyard, MA, here are the 4 best family friendly rentals

Chappy Whispering Pines - Martha's Vineyard, MA
9.9 19 reviews
Martha's Vineyard, MA
07/05 – 07/12
$519/nighttotal: $3633 (7 )

Chappy Whispering Pines

4 4
apartment , Edgartown
This four-bedroom Edgartown vacation rental is located on Chappaquiddick Island, a short distance (0.75 miles) from Dyke Bridge Beach and a mile from Wasque Reservation, with easy ferry access (2.7 miles) to Edgartown Village.
The 4-bedroom home features two full bathrooms, a mahogany outdoor shower, two decks, a screened porch, and accommodates eight guests, offering free parking and proximity to kayaking, biking, and hiking trails.
New 4 Br House Near Center And Beaches With Bikes - Martha's Vineyard, MA
10 7 reviews
Martha's Vineyard, MA
08/27 – 09/03
$1479/nighttotal: $10353 (7 )

New 4 Br House Near Center And Beaches With Bikes

4 6
apartment , Edgartown
This charming home is situated in Katama, a peaceful neighborhood in Edgartown, just a short drive from the city center, South Beach, and the famous gingerbread houses on the main square. This cozy retreat offers a comfortable and spacious living experience for families and friends.
The home features four bedrooms, three bathrooms, and can accommodate up to nine guests. Enjoy the fully equipped kitchen, outdoor barbecue, fire pit, and access to bikes, chairs, and beach towels for a relaxing and enjoyable vacation.
Charming Cottage With Deck, Yard, & Ac - Walk To Beach, Main Street, & Ferry - Martha's Vineyard, MA
9.6 61 reviews
Martha's Vineyard, MA
07/05 – 07/12
$739/nighttotal: $5173 (7 )

Charming Cottage With Deck, Yard, & Ac - Walk To Beach, Main Street, & Ferry

3 4
apartment , Falmouth
This Falmouth Heights cottage is a short walk to Falmouth Heights Beach, Main Street shops and restaurants, and the Woods Hole Ferry Terminal.
This 1670 square foot home accommodates up to 6 guests with 3 bedrooms and 3 bathrooms, featuring a well-equipped kitchen with stainless steel appliances, air conditioning, a garden, and an outdoor deck.
Beautiful 5 Br, 4.5 Baths W/ Modern Conveniences - Martha's Vineyard, MA
10 14 reviews
Martha's Vineyard, MA
07/05 – 07/12
$1812/nighttotal: $12684 (7 )

Beautiful 5 Br, 4.5 Baths W/ Modern Conveniences

5 4
apartment , Oak Bluffs
This Oak Bluffs vacation home is conveniently located within a 10-minute walk of the town's hospital and landmarks, offering a private garden with barbecue grills and a smoke-free environment. With an excellent user rating, the house offers a 5-bedroom, 5-bathroom layout with a floor area of 3000 square feet, accommodating up to 10 guests. Amenities include a fully equipped kitchen with essential appliances, free WiFi, a DVD player, and air conditioning.

Where to stay in Martha's Vineyard?

Edgartown

Edgartown is the island's largest town, founded in 1642. For sailing enthusiasts, it is an ideal place, since it has a harbor and the famous Edgartown Lighthouse. Among its places of interest is the Whaling Museum. The town is a 20-minute drive from the Martha's Vineyard airport.

Oak Bluffs

Oak Bluffs is a town known for its small log cabins that are part of a Methodist camp, known as Cottage City. The town also has attractions such as the famous Inkwell Beach and the Flying Horses Carousel amusement park.

Vineyard Haven

Vineyard Haven is the main port and commercial center of the island, where ferries arrive from the mainland, and is only a 10-minute drive from the Martha's Vineyard airport. It has a quiet, family-friendly atmosphere and among its streets is the Martha's Vineyard Maritime Museum, which displays artifacts related to sailing and fishing on the island.

West Tisbury

West Tisbury is a rural village located between farms and forests. It is the ideal place for nature lovers, as it has several nature reserves and trails such as Manuel F. Correllus. It is also known for holding an annual agricultural fair, which offers animal exhibits, crafts and local cuisine.

Chilmark

Chilmark is known for its impressive cliffs and white sandy beaches. It is an ideal place for those seeking privacy and relaxation, as it has few houses and commercial establishments. The town is also famous for the Wampanoag Indian Museum, where you can learn about the culture and history of the island's Native Americans.

Aquinnah

Aquinnah is the most remote village on the island, located about 35 minutes drive from the airport and is inhabited mainly by the indigenous Wampanoag people. It is an impressive place for its red clay cliffs, which contrast with the colors of the forest and the sea. It also has one of the few remaining nudist beaches in the United States, called Moshup Beach.

Best Martha's Vineyard, MA vacation rentals with a pool

Among the 1635 accommodations in Martha's Vineyard, MA, here are the 4 best rentals with a pool

Winnetu Oceanside Resort At South Beach - Martha's Vineyard, MA
9.8 41 reviews
Martha's Vineyard, MA
07/01 – 07/05
$2144/nighttotal: $8576 (4 )

Winnetu Oceanside Resort At South Beach

1 4
resort , Edgartown
Winnetu Oceanside Resort At South Beach in Edgartown offers an excellent location at South Beach, a renowned coastal landmark on the island.
This resort provides home-like accommodations with thoughtfully designed spaces and bathroom amenities, ensuring guest contentment, and is located at South Beach, offering proximity to the island's coastline.
Cape Cod Falmouth Getaway, Great Harbors, Pool, Close Beaches Aug 10-16 Avail - Martha's Vineyard, MA
10 38 reviews
Martha's Vineyard, MA
07/05 – 07/10
$595/nighttotal: $2975 (5 )

Cape Cod Falmouth Getaway, Great Harbors, Pool, Close Beaches Aug 10-16 Avail

3 2
apartment , Falmouth
This family-friendly vacation home in East Falmouth, just 2 miles from Cape Cod Beaches and Menauhant Beach, is an excellent choice for travelers visiting Falmouth. It has received an excellent user rating.
The house has 3 bedrooms, 2 bathrooms, and a floor area of 1400 square feet. It can accommodate up to 8 guests. Amenities include an outdoor pool, garden, barbecue grills, and free WiFi. It also features a fully equipped kitchen, a patio, and a smoke-free environment.
Oak Bluffs Allure - Martha's Vineyard, MA
Martha's Vineyard, MA
08/16 – 08/20
$4630/nighttotal: $18520 (4 )

Oak Bluffs Allure

1 2
apartment , Oak Bluffs
This bespoke estate in Oak Bluffs features a main residence and a separate guest home, offering a private oasis with a heated swimming pool and hot tub, all within convenient proximity to the island's attractions. This luxurious 4-bedroom, 4-bathroom villa accommodates up to 8 guests and boasts high-end finishes, top-tier appliances, and expansive grounds, providing a complete and private experience for your island getaway.
Relax & Unwind: Poolside Marthas Vineyard Stay - Martha's Vineyard, MA
Martha's Vineyard, MA
07/01 – 07/05
$3381/nighttotal: $13524 (4 )

Relax & Unwind: Poolside Marthas Vineyard Stay

5 4
apartment , Oak Bluffs
This Oak Bluffs vacation home is situated a short drive from Martha's Vineyard Preservation Trust Historic Buildings, located 11 minutes away, offering convenient access to local attractions.
This spacious 2930 square foot residence accommodates up to 10 guests with 5 bedrooms and 5 bathrooms, featuring a private swimming pool, a terrace with a fire pit, Wi-Fi, and a fully equipped kitchen.

Frequently Asked Questions about vacation rentals in Martha's Vineyard, MA

  • What are the must-see sights on Martha's Vineyard, MA, United States?

    For must-see sights on Martha's Vineyard, you definitely want to check out the charming towns of Oak Bluffs with its iconic gingerbread cottages and the Flying Horses Carousel, Edgartown with its historic harbor and stately homes, and Vineyard Haven, a bustling port town. A visit to the Gay Head Cliffs on Aquinnah is a must for their dramatic clay cliffs and stunning ocean views. Don't miss the Martha's Vineyard Museum for a deeper dive into the island's history and culture.
  • What are the best Airbnb and vacation rentals in Martha's Vineyard, MA?

  • Are there unique natural phenomena on Martha's Vineyard, MA, United States?

    Absolutely! The Gay Head Cliffs, with their colorful layers of clay, are a unique geological formation. The island's diverse beaches, from the wide sands of South Beach to the dramatic cliffs of Aquinnah, also offer unique natural beauty. You'll find various wildlife, including seals and shorebirds, depending on the season.
  • What are the most popular Airbnbs in Martha's Vineyard, MA?

  • What essentials should you bring along for a trip to Martha's Vineyard, MA, United States?

    Pack light clothing, swimwear, comfortable walking shoes, sunscreen, insect repellent, and a light jacket or sweater, even in summer, as evenings can get cool. Don't forget sunglasses and a hat for sun protection. If you plan on biking, bring a helmet. A reusable water bottle is a good idea, as well as a camera to capture the stunning scenery.
  • What are the best vacation rentals with a pool in Martha's Vineyard, MA?

  • What famous events or festivals are happening on Martha's Vineyard, MA, United States?

    Martha's Vineyard hosts many events throughout the year. The annual Agricultural Fair is a popular event, showcasing local produce and livestock. The Island's various towns also host their own smaller festivals and events throughout the summer months. Check local listings for specific dates and events.
  • What are the best rentals for families and kids in Martha's Vineyard, MA?

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) on Martha's Vineyard, MA, United States?

    A daily budget for Martha's Vineyard can vary greatly depending on your travel style. Expect to spend at least $200-$300 per person per day for mid-range accommodations, meals, and activities. Luxury travel will obviously be significantly higher. Transportation costs will depend on whether you rent a car or use other means of transport like taxis or the Vineyard Transit Authority bus system.
  • What are the best rentals or Airbnbs with a jacuzzi in Martha's Vineyard, MA?

    The best vacation rentals or Airbnb with a jacuzzi in Martha's Vineyard, MA are Victorian Oasis: Driveway - Hot Tub - Grill & More, Large Downtown Captain's House 9bd and Mermaid Cottage.

  • Where can you find the best restaurants serving local dishes on Martha's Vineyard, MA, United States, and what are the must-try specialties?

    The Black Dog Tavern in Vineyard Haven is a classic for its casual atmosphere and seafood. The Seafood Shanty in Oak Bluffs is another popular spot known for its fresh seafood. Many restaurants feature locally sourced seafood, like lobster rolls and clam chowder. You can also find farm-to-table options showcasing the island's agricultural bounty.
  • What are some less-famous attractions on Martha's Vineyard, MA, United States that are worth the visit?

    The Alley's General Store in Menemsha is a charming spot with a unique history. Exploring the various smaller beaches away from the main tourist areas can offer a more tranquil experience. Consider a visit to the Menemsha Fish Market to watch the fishing boats come in and get a feel for the local fishing industry. The Wampanoag Tribe of Gay Head (Aquinnah) cultural center offers a glimpse into the island's indigenous history.
  • What are the best activities for engaging with locals and understanding their culture on Martha's Vineyard, MA, United States?

    Visiting local farmers' markets is a great way to interact with residents and sample local produce. Attending a town meeting offers a unique insight into the island's governance. Spending time in smaller, less touristy towns allows for more authentic interactions with residents. Striking up conversations with shopkeepers and restaurant staff can also be very rewarding.
  • What unique natural landscapes and terrain features can travelers explore on Martha's Vineyard, MA, United States?

    Martha's Vineyard boasts diverse landscapes. The dramatic cliffs of Aquinnah, the rolling hills of the island's interior, the sandy beaches, and the various ponds and salt marshes all offer unique exploration opportunities. Consider hiking or biking the many trails throughout the island.
  • How many days are ideal for visiting Martha's Vineyard, MA, United States, and what are some itinerary suggestions?

    Three to four days is a good amount of time to explore the highlights of Martha's Vineyard. A possible itinerary could include: Day 1: Exploring Oak Bluffs and Vineyard Haven; Day 2: Visiting Edgartown and the Martha's Vineyard Museum; Day 3: Exploring Aquinnah and the Gay Head Cliffs; Day 4: Relaxing on the beach and enjoying the island's atmosphere. This is just a suggestion; adjust it based on your interests.
  • How is the weather on Martha's Vineyard, MA, United States in high season?

    High season (summer) on Martha's Vineyard is typically warm and sunny, with average highs in the 70s and 80s Fahrenheit (low to mid 20s Celsius). However, it's always a good idea to pack layers, as evenings can be cooler, and there's always a chance of a shower.

Nearby regions

Best Martha's Vineyard, MA vacation rentals with a balcony

Modern Coastal Katama Retreat - 4th Season Of 5 Star Summers - Martha's Vineyard, MA
10 21 reviews
Martha's Vineyard, MA
07/05 – 07/12
$2813/nighttotal: $19691 (7 )

Modern Coastal Katama Retreat - 4th Season Of 5 Star Summers

3 4
apartment , Edgartown
This Edgartown vacation home is ideally situated less than a mile from Katama Farm, Katama Plains Natural Heritage Area, and Huckleberry Barrens, and within two miles of South Beach State Park and Katama Point.
This three-bedroom, four-bathroom house comfortably sleeps seven guests and boasts a fully equipped kitchen, a fitness center, a terrace, and a relaxing garden with barbecue grills, offering modern amenities including Wi-Fi and an espresso maker.
Waterfront, Privacy And Tranquility On Tisbury Great Pond - Martha's Vineyard, MA
9.9 35 reviews
Martha's Vineyard, MA
07/05 – 07/12
$1539/nighttotal: $10773 (7 )

Waterfront, Privacy And Tranquility On Tisbury Great Pond

3 4
farm , Chilmark
This Chilmark gîte is located on the waterfront, close to art galleries, a general store, and a renowned arboretum. It has received excellent ratings for location, cleanliness, and overall user experience. This spacious vacation rental offers 2,300 square feet of living space with three bedrooms, three bathrooms, and a capacity for six guests. Amenities include a fully equipped kitchen, air conditioning, a Jacuzzi, a terrace, a garden, a fitness center, and parking.
Garage Suite - Martha's Vineyard, MA
10 1 review
Martha's Vineyard, MA
07/05 – 07/10
$625/nighttotal: $3125 (5 )

Garage Suite

1 2
apartment , Oak Bluffs
This Oak Bluffs apartment rental is conveniently located near Oak Bluffs' attractions and offers easy access to local cycling paths and a children's playground.
The 500-square-foot unit features one bedroom, one bathroom, a fully equipped kitchen with dining area, a terrace, air conditioning, and sleeps up to three guests.
Sea Captain's Estate In Falmouth Village - Martha's Vineyard, MA
10 2 reviews
Martha's Vineyard, MA
08/13 – 08/15
$2973/nighttotal: $5946 (2 )

Sea Captain's Estate In Falmouth Village

7 2
apartment , Falmouth
This 7-bedroom, 7-bathroom estate and guest house in Falmouth is a short walk from Falmouth Village's Main Street, offering convenient access to Woods Hole, the Martha's Vineyard Ferry, and the Shining Sea Bikeway, and is just 0.9 miles from Surf Drive Beach. The property accommodates up to 16 guests with six en-suite bedrooms in the Main House and a separate Guest House, featuring a full kitchen, dishwasher, microwave, fridge, air conditioning, a terrace/balcony, garden, fire pit, and on-site bike rentals.

Best Martha's Vineyard, MA vacation rentals with parking

Serene 6-bedroom Vineyard Haven Retreat - Martha's Vineyard, MA
Martha's Vineyard, MA
08/27 – 09/03
$6079/nighttotal: $42553 (7 )

Serene 6-bedroom Vineyard Haven Retreat

6 6
apartment , Tisbury
This 6-bedroom, 5-bathroom vacation home in Vineyard Haven, Tisbury, offers a 14-minute walk to Lake Tashmoo and is a 3-minute drive from Tisbury Town Beach.
This expansive rental accommodates up to 12 guests with amenities including a swimming pool, Wi-Fi, a garden, and on-site parking, conveniently located a 4-minute drive from the Martha's Vineyard Film Center and a 5-minute drive from the Martha's Vineyard Museum.
Irene's Hideaway - Martha's Vineyard, MA
Martha's Vineyard, MA
07/05 – 07/12
$1346/nighttotal: $9422 (7 )

Irene's Hideaway

4 4
apartment , Tisbury
This Tisbury condominium is located at the end of a private road, just over a mile from Tashmoo Beach and minutes from Main Street shopping and dining, Lake Street Landing, and the Vineyard Haven ferry terminal.
This 4-bedroom, 3-bathroom residence accommodates up to 8 guests and features a modern kitchen with a dishwasher, air conditioning, a garden, parking, and an expansive mahogany deck for outdoor enjoyment.
Falmouth Family Home: Beach, Fire Pit & Games! - Martha's Vineyard, MA
Martha's Vineyard, MA
08/05 – 08/09
$1397/nighttotal: $5588 (4 )

Falmouth Family Home: Beach, Fire Pit & Games!

4 2
apartment , Falmouth
This 3-bedroom, 2-bathroom condo in downtown East Falmouth offers 1600 square feet of living space and accommodates up to 10 guests, featuring air conditioning, a garden, and parking.
Conveniently located near the beach, Main Street, the College Light Opera Company, the Cape Cod Children's Museum, and Mashpee River Reservation, this family-friendly residence provides a fully equipped kitchen with a dishwasher and refrigerator, along with proximity to activities like Stand Up & Paddle Cape Cod.
Downtown Captain's Mansion- The Dexter- Family, Event, And Pet Friendly - Martha's Vineyard, MA
10 131 reviews
Martha's Vineyard, MA
07/05 – 07/10
$3575/nighttotal: $17875 (5 )

Downtown Captain's Mansion- The Dexter- Family, Event, And Pet Friendly

9 2
apartment , Tisbury
This mansion sits on Main Street in Vineyard Haven, just a short 5-minute walk from the ferry and within easy reach of all the town's amenities. The property has earned excellent ratings for user experience, location, and cleanliness.
This spacious home has 9 bedrooms, sleeping 18 people, and covers 6,800 square feet. Guests can enjoy a chef's kitchen, multiple living spaces, a private patio, two decks, an outdoor shower, and a jacuzzi.
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