Best Vacation Homes in Vineyard Haven
House
10.0(92 Reviews)
2 Bedrooms
2 Baths
5 Guests
1400 ft²
Hot Tub
Parking
Balcony/Terrace
Kitchen
R10,394/Night
7 Nights - R72,755
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
10763.91 ft²
View
Air Conditioner
Internet
Child Friendly
R12,708/Night
7 Nights - R88,959
R11,484/Night
7 Nights - R80,380
New
Apartment
10.0(83 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Hot Tub
- Parking
Ocean View- Balcony/Terrace
R4,539/Night
7 Nights - R31,771
House
10.0(1 Review)
3 Bedrooms
1 Bath
6 Guests
2787.85 ft²
- Parking
- View
- Internet
- Child Friendly
R8,210/Night
7 Nights - R57,472
House
10.0(63 Reviews)
2 Bedrooms
1 Bath
5 Guests
600 ft²
Oceanfront- Parking
- Ocean View
- Balcony/Terrace
R7,479/Night
7 Nights - R52,355
House
10.0(62 Reviews)
2 Bedrooms
2 Baths
6 Guests
1615 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
R19,494/Night
7 Nights - R136,448
House
10.0(61 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R6,357/Night
7 Nights - R44,496
Vineyard Haven Luxury Rentals
House
9.8(17 Reviews)
6 Bedrooms
5 Baths
16 Guests
7000 ft²
Private Pool- Oceanfront
- Hot Tub
- Parking
R154,093/Night
7 Nights - R1,078,656
House
10.0(6 Reviews)
7 Bedrooms
6 Baths
12 Guests
- Private Pool
- Hot Tub
- Parking
Pool
R111,482/Night
7 Nights - R780,377
House
6 Bedrooms
3 Baths
14 Guests
- Private Pool
- Parking
- Pool
Spa
R82,270/Night
7 Nights - R575,890
House
10.0(2 Reviews)
6 Bedrooms
5 Baths
12 Guests
4964 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R75,299/Night
7 Nights - R527,096
House
10.0(1 Review)
5 Bedrooms
6 Baths
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
R74,888/Night
7 Nights - R524,220
House
6 Bedrooms
5 Baths
12 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R68,898/Night
7 Nights - R482,282
House
4 Bedrooms
4 Baths
7 Guests
- Private Pool
- Parking
- Pool
- Ocean View
R55,319/Night
7 Nights - R387,237
House
10.0(1 Review)
5 Bedrooms
4 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R38,800/Night
7 Nights - R271,608
Vineyard Haven Pet Friendly Vacation Rentals
Cottage
10.0(33 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R12,804/Night
7 Nights - R89,627
Apartment
8.0(15 Reviews)
2 Bedrooms
2 Baths
7 Guests
1291.67 ft²
- Balcony/Terrace
- View
- Air Conditioner
- Internet
R8,111/Night
7 Nights - R56,770
Condo
10.0(1 Review)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R13,186/Night
7 Nights - R92,303
House
8.0(14 Reviews)
1 Bedroom
1 Bath
4 Guests
1001.04 ft²
- Balcony/Terrace
- View
- Air Conditioner
- Internet
R10,836/Night
7 Nights - R75,849
House
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
1000 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R6,065/Night
7 Nights - R42,456
House
9.8(16 Reviews)
2 Bedrooms
1 Bath
6 Guests
700 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
R5,990/Night
7 Nights - R41,938
House
9.4(50 Reviews)
2 Bedrooms
1 Bath
4 Guests
1100 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R5,865/Night
7 Nights - R41,051
New
Apartment
2 Bedrooms
2 Baths
7 Guests
1296 ft²
- Oceanfront
- Ocean View
- View
- Kitchen
R8,858/Night
7 Nights - R62,003
Vineyard Haven Large Vacation Homes
House
10.0(90 Reviews)
5 Bedrooms
4 Baths
10 Guests
3600 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
R14,550/Night
7 Nights - R101,851
House
9.4(6 Reviews)
5 Bedrooms
2 Baths
8 Guests
1797.57 ft²
- Oceanfront
- Parking
- Ocean View
- View
R4,565/Night
7 Nights - R31,955
House
10.0(6 Reviews)
6 Bedrooms
3 Baths
16 Guests
3300 ft²
R17,603/Night
7 Nights - R123,221
House
10.0(71 Reviews)
9 Bedrooms
6 Baths
18 Guests
6800 ft²
- Oceanfront
Breakfast- Parking
- Ocean View
R34,722/Night
7 Nights - R243,064
House
6.0(1 Review)
1 Bedroom
4 Baths
10 Guests
2002.09 ft²
- Balcony/Terrace
- Child Friendly
Restaurant
Laundry
R15,735/Night
7 Nights - R110,145
House
10.0(60 Reviews)
6 Bedrooms
3 Baths
11 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R18,964/Night
7 Nights - R132,752
House
10.0(58 Reviews)
4 Bedrooms
2 Baths
10 Guests
3500 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
R13,323/Night
7 Nights - R93,256
House
10.0(43 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R18,594/Night
7 Nights - R130,160
Why Choose Rent By Owner for your Vineyard Haven Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Vineyard Haven Vacation Rentals
Where are the best neighborhoods to stay in Vineyard Haven?
When visiting Vineyard Haven, Massachusetts, choosing the right neighborhood to stay in can enhance your overall experience. Located on Martha's Vineyard, Vineyard Haven offers a variety of charming neighborhoods that cater to different preferences, whether you seek proximity to local shops, serene waterfront views, or easy access to ferry terminals. Exploring accommodations in this area allows you to enjoy the authentic coastal atmosphere, with many properties offering comfortable amenities and convenient locations. By selecting a well-situated rental in Vineyard Haven, you ensure a relaxing and memorable stay on Martha’s Vineyard, making it easier to discover everything this picturesque island has to offer.
West Chop
Settled in the scenic region of Vineyard Haven, this area offers peaceful surroundings and charming coastal views, making it an ideal spot for a relaxing getaway. Here, you can enjoy a tranquil environment while exploring the natural beauty that defines this part of the island.
View 661+ Rentals in West ChopBest Times to Visit Vineyard Haven
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit ensures you experience the best of this destination, with pleasant weather and fewer crowds, making your stay in Vineyard Haven's vacation rentals truly memorable.
Peak Season Highlights
Summer (June to August)
This is the busiest time of year, when the area sees warm weather and lively local activities, making it ideal for enjoying the scenic beauty and maritime charm of this destination.
Average Temperature Daytime: 75-85°F - Nighttime: 60-70°F
Fall (September to October)
During these months, the region showcases stunning foliage and pleasant temperatures, attracting visitors seeking a picturesque autumn experience and outdoor exploration.
Average Temperature Daytime: 65-75°F - Nighttime: 50-60°F
Off-Season Highlights
Spring (April to May)
In spring, the area begins to bloom with mild weather that offers a quieter atmosphere, providing a relaxing setting for those looking to avoid the crowds while exploring nature at its finest.
Average Temperature Daytime: 55-65°F - Nighttime: 40-50°F
Winter (November to March)
The winter months bring a serene and less crowded environment, perfect for travelers who prefer tranquility and are interested in experiencing the region's peaceful off-season charm.
Average Temperature Daytime: 30-45°F - Nighttime: 20-30°F
Weekly Weather Forecast for Vineyard Haven
How to Book Your Vineyard Haven Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Vineyard Haven
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor space with a spacious patio or deck for relaxing and entertaining.
- Take advantage of lush gardens or landscaped yards that enhance the outdoor ambiance.
- Make use of outdoor dining areas perfect for savoring meals al fresco during your stay.
- Relax in a well-maintained backyard with seating arrangements ideal for gatherings under the sun or stars.
- Utilize outdoor grills or barbecues to prepare delicious meals while enjoying the fresh air.
- Discover access to nearby outdoor recreation areas, such as parks or walking trails, for outdoor adventures.
- Benefit from convenient parking facilities in a quiet outdoor setting, enhancing your overall experience here.
Top Attractions Around Vineyard Haven
What attractions are nearby?
In this charming destination, you can enjoy a variety of nearby activities such as exploring scenic beaches, visiting local shops, and immersing yourself in the vibrant community atmosphere that the region offers.
Family Activities
- Flying Horses Carousel: Experience a classic family activity at this historic carousel, offering nostalgic fun right in the area.
- Island Grown Farm Tour: Explore local farms to learn about sustainable agriculture and enjoy fresh, farm-grown produce during your stay.
- Vineyard Haven Harbor Walk: Stroll along the scenic harbor, watching boats come and go while soaking in the charming coastal atmosphere perfect for all ages.
- Local Art Galleries & Studios: Discover vibrant regional art within the region's galleries, encouraging creativity and family engagement in this artistic community.
Adult Activities
- Wine Tasting Tours: Explore local wineries and indulge in wine tasting experiences that highlight the region's renowned vineyards.
- Harbor Cruises: Take a scenic boat cruise around the harbor to enjoy stunning views and learn about the area's maritime history.
- Art Galleries and Studios: Visit diverse art galleries showcasing local talent, offering a vibrant cultural experience in this charming destination.
- Private Beach Access: Relax at nearby beaches with your own exclusive access, perfect for sunbathing or enjoying a peaceful seaside walk.
Other Places to Stay in Vineyard Haven, MA
Martha's Vineyard
Martha's Vineyard Museum
Island Cove Adventures
Martha's Vineyard Film Center
Martha's Vineyard Chamber of Commerce
Vineyard Playhouse
Island Cove Miniature Golf
Vineyard Haven Public Library
West Chop
Tisbury
Lake Tashmoo
West Tisbury
Vineyard Haven Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Markets and Food Scene: Take the time to visit nearby farmers' markets and eateries to experience authentic flavors that showcase the region's culinary culture.
- Plan Outdoor Activities: Make the most of your stay by engaging in local outdoor pursuits such as walking along scenic waterfronts or exploring lush parks in the area.
- Discover Unique Art and Craft Shops: Browse through charming shops featuring handmade crafts and artwork that reflect this destination's creative spirit.
- Enjoy Convenient Access to Transportation: Arrange for transportation options early to easily navigate here and maximize your time exploring all that the region offers.
Transportation Options
- Ferry Service: Regular ferries connect this area to nearby islands and the mainland, offering a scenic and convenient way to explore the region.
- Taxi and Rideshare Services: Local taxi companies and rideshare options provide flexible transportation for getting around conveniently within this destination.
- Car Rentals: Several rental agencies available here allow you to explore the town and surrounding areas at your own pace with ease.
- Public Transit Buses: Local bus routes serve key points in the region, making it an economical choice for exploring without a vehicle.
Local Customs Options
- Local Seafood Traditions: You can indulge in the region’s renowned seafood customs, highlighting fresh catches and maritime culinary practices.
- Harbor Celebrations: Participating in harbor festivals or observing boat parades offers a glimpse into the community’s nautical heritage.
- Artisan Craftsmanship: Supporting local artisans by exploring craft markets showcases the area’s unique artistic traditions rooted in its coastal culture.
- Historical Preservation: Respect for historic sites and architecture reflects the region’s commitment to maintaining its rich maritime history.
Frequently Asked Questions About Vineyard Haven?
1. What are the top vacation rentals in Vineyard Haven?
There are a lot of options in Vineyard Haven. If you plan on staying in the Vineyard Haven area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Vineyard Haven:
- Charming, Clean And Well Maintained Home Walking Distance To Town And Beach
- Contemporary Pet-Friendly Year-round Retreat. In the Woods, Walk to Town.
- Close to Lambert's Cove Beach. Pastoral setting. Elegant farmhouse & guest house
- Sea Captain's Victorian studio bedroom apartment. Pets OK
- Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly
- Classic Downtown Property
- Well-Appointed 3 bedrm 4 bathrm with AC and 50+ 5-star reviews!
- Lambert's Cove Beach Getaway - NEW LISTING Private Beach Access!
- Vineyard Haven Beach House
- FABULOUS Makonikey OCEANFRONT With Private Beach !Wrap Around Deck, Pets Ok, A/C
2. How many vacation rentals have private pools in Vineyard Haven?
There are 11 vacation rentals with private pools near Vineyard Haven. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Vineyard Haven are best for families?
If you are looking for a family-friendly vacation home in Vineyard Haven, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Vineyard Haven:
4. How many Rentbyowner vacation rentals are available in Vineyard Haven?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 429 in the Vineyard Haven area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Vineyard Haven.
5. What is the cancellation policy for vacation rentals in Vineyard Haven, Massachusetts?
The cancellation policy varies depending on the specific listing you choose. It is important to review the property's cancellation terms directly on the listing page or contact the property owner for detailed information before booking.
6. How do I book a vacation rental in Vineyard Haven, Massachusetts?
You can easily secure your stay by selecting your preferred dates and contacting the property owner through the listing. Be sure to read all details and reach out with any questions to ensure a smooth booking process.
7. Are there any house rules or restrictions I should be aware of in this destination's vacation rentals?
Each property has its own set of house rules and restrictions, which are typically listed on the property page. Reviewing these carefully will help ensure your stay conforms to the owner’s requirements.
8. What amenities are usually included in vacation rentals here?
Amenities vary by property but often include essentials like Wi-Fi, parking, kitchens, and outdoor spaces. Specific amenities are detailed in each listing, so check those before confirming your reservation.
9. Is there a minimum stay requirement for vacation rentals in this area?
Many listings specify a minimum stay requirement, especially during peak seasons. Confirm this detail on the particular property listing or by contacting the owner directly to avoid surprises.
Vineyard Haven Top Rated Vacation Rentals
House
10.0(25 Reviews)
4 Bedrooms
4 Baths
9 Guests
2400 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
R35,812/Night
7 Nights - R250,689
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
2016 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
R14,669/Night
7 Nights - R102,687
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
R14,186/Night
7 Nights - R99,309
House
10.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
1600 ft²
- Private Pool
- Parking
- Pool
- Ocean View
R19,403/Night
7 Nights - R135,812
House
9.6(38 Reviews)
3 Bedrooms
2 Baths
7 Guests
1800 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R4,760/Night
7 Nights - R33,326
R8,200/Night
7 Nights - R57,405
New
Apartment
9.2(5 Reviews)
1 Bedroom
1 Bath
2 Guests
571 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
R5,387/Night
7 Nights - R37,707
Hotel
9.0(691 Reviews)
1 Bath
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R7,627/Night
7 Nights - R53,392
