A coastal cliff with a sandy beach and the ocean.

Aquinnah Vacation Rentals

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Our top choices for Aquinnah vacation rentals

1. Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool
Chilmark
9.6 out of 10, Exceptional, (26 reviews)
"This is a great property for an individual or a couple looking to explore the island!"
United States
Jillian G.
The price is CA $562
CA $854 total
includes taxes & fees
Oct 13 - Oct 14
Cozy efficiency apartment/heated pool

2. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
10.0 out of 10, Exceptional, (32 reviews)
"This property is quiet yet close enough to the business areas. Very clean, well maintained lovely unit with balcony. The host Joziane commutated with us from minutes after the booking to the end of stay, very helpful."
United States
Unspecified U.
The price is CA $381
CA $761 total
includes taxes & fees
Oct 15 - Oct 16
Brand new! Lovely apartment-Vineyard Haven

3. Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Tisbury
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful view of the lagoon; ideal place for a couple or single. Leisurely walk to town and close to public transportation."
United States
Adrienne W.
The price is CA $413
CA $743 total
includes taxes & fees
Oct 12 - Oct 13
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

4. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (9 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is CA $704
CA $1,533 total
includes taxes & fees
Oct 31 - Nov 1
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

5. Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs 4BR • 5 Min Drive to Downtown
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"This place was just what we needed! Would definitely stay again. Cozy and feels very homey! Thanks!"
United States
Chris S.
The price is CA $511
CA $1,197 total
includes taxes & fees
Oct 4 - Oct 5
Oak Bluffs 4BR • 5 Min Drive to Downtown

6. Backyard Retreat / 5 Min > Beach & Main St

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is CA $275
CA $892 total
includes taxes & fees
Oct 6 - Oct 7
Backyard Retreat / 5 Min > Beach & Main St

7. Walk to Beach & Lighthouse: Oak Bluffs Studio!

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
7.8 out of 10, Good, (12 reviews)
"The unit was clean and sufficient for 2 people. Outside could use some attention."
United States
Donna R.
The price is CA $468
CA $871 total
includes taxes & fees
Oct 31 - Nov 1
Walk to Beach & Lighthouse: Oak Bluffs Studio!

8. New 4 BR house near center and beaches with bikes

New 4 BR house near center and beaches with bikes
Katama
9.8 out of 10, Exceptional, (11 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is CA $754
CA $2,070 total
includes taxes & fees
Oct 11 - Oct 12
New 4 BR house near center and beaches with bikes

9. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
7.0 out of 10, Good, (12 reviews)
"Loved this spot. Perfect central island location. Fantastic owner with an incredible response time. Would recommend this property to all5 stars"
United States
Eli R.
The price is CA $450
CA $1,018 total
includes taxes & fees
Oct 4 - Oct 5
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

10. Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and comfy place, a short drive to Falmouth center! Communication was very easy and check-in simple."
United States
Harry H.
The price is CA $231
CA $344 total
includes taxes & fees
Oct 4 - Oct 5
Charming studio in tranquil Falmouth with AC

11. Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!

Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!
Dartmouth
10.0 out of 10, Exceptional, (2 reviews)
"Great location. Near ButtonWood Park. Quiet neighborhood. Enjoyed my stay."
United States
richard m.
The price is CA $186
CA $464 total
includes taxes & fees
Oct 22 - Oct 23
Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!

12. Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Oak Bluffs
9.4 out of 10, Exceptional, (96 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
The price is CA $384
CA $706 total
includes taxes & fees
Oct 4 - Oct 5
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

13. Charming Guesthouse | Walk to Beach | Downtown

Charming Guesthouse | Walk to Beach | Downtown
Falmouth
10.0 out of 10, Exceptional, (1 review)
"The house was very convenient to the beach, Aldi’s, Walmart, and local restaurants & shops. I wasn’t sure how private it was being a guest house, but I never felt that we didn’t have privacy. Our dogs enjoyed the little fenced in yard. We appreciated the updated bathroom and kitchen. The weather was so pleasant a small outdoor area would have been nice, and we missed not having a washer & dryer and dishwasher, but overall it was clean and cozy. We would stay there again! We loved the Cape,...
United States
Kandy W.
The price is CA $280
CA $919 total
includes taxes & fees
Oct 4 - Oct 5
Charming Guesthouse | Walk to Beach | Downtown

14. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Oak Bluffs
9.8 out of 10, Exceptional, (9 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is CA $566
CA $1,945 total
includes taxes & fees
Oct 31 - Nov 1
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

15. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is CA $302
CA $1,110 total
includes taxes & fees
Oct 8 - Oct 9
West Falmouth Family Retreat Near Chapoquoit Beach

16. Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
Dartmouth
10.0 out of 10, Exceptional, (17 reviews)
"This property was beautiful, peaceful, and so relaxing! The communication and check-in were effortless, the house was spotless, and the views were fabulous! We definitely want to return!"
United States
Judith M.
The price is CA $448
CA $742 total
includes taxes & fees
Oct 11 - Oct 12
Charming cottage overlooking the bay in Padanaram Village.

17. Cozy Cottage walk to Menauhant Beach

Cozy Cottage walk to Menauhant Beach
East Falmouth
8.8 out of 10, Excellent, (8 reviews)
"It was a great weekend spot. Had everything we needed, nicely decorated, and in a great and private location"
United States
Grace P.
The price is CA $335
CA $1,170 total
includes taxes & fees
Oct 8 - Oct 9
Cozy Cottage walk to Menauhant Beach

18. Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (224 reviews)
"Great location "
United States
Stephanie B.
The price is CA $256
CA $728 total
includes taxes & fees
Nov 1 - Nov 2
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

19. Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
10.0 out of 10, Exceptional, (3 reviews)
"Brenda and Derek were amazing hosts. They have a beautifully landscaped property with all the amenities needed for a relaxing family vacation. They are super responsive and take a lot of pride in giving their guests a top-notch experience. We will definitely consider staying at their properties again."
United States
Lamar A.
The price is CA $3,559
CA $5,405 total
includes taxes & fees
Oct 12 - Oct 13
Beautiful Estate with salt water pool & pond with kayaks

20. LUX on Main | Downtown | Parking | Sleeps 6, #201

LUX on Main | Downtown | Parking | Sleeps 6, #201
Falmouth
10.0 out of 10, Exceptional, (6 reviews)
"This was the perfect location for our Cape Cod getaway. It was very central to everything we were doing while down there, very effortless to get to Martha’s Vineyard as well! The location was perfect with a bunch of different restaurants, shops and other stores all in walking distance. We will definitely consider staying here again in the future!"
United States
Zack D.
The price is CA $347
CA $1,133 total
includes taxes & fees
Oct 5 - Oct 6
LUX on Main | Downtown | Parking | Sleeps 6, #201
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Aquinnah Hotel Reviews

Find out more about Aquinnah

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Aquinnah. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Aquinnah?

Yes, we give you a choice of vacation rentals near popular local attractions in Aquinnah, or you can go with a more remote option if you're looking for relaxation. Aquinnah is known for its wineries and beaches. Make sure you have time to check out the local tours and parks during your trip.

What are some of the best vacation home rentals that Aquinnah has to offer?

Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel: This vacation home near Aquinnah is located near the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Aquinnah?

With 32 Expedia vacation rentals, you're sure to find just the right place for your Aquinnah stay.

What can I see and do in Aquinnah?

Aquinnah Cliffs and Squibnocket Pond are a couple of lovely local spots to get outside and enjoy nature. While here, Gay Head Lighthouse and Long Beach are other places worth a visit.

What are vacation rentals like in Aquinnah?

Vacation rentals are private properties you can book for several days or more in Aquinnah. Vacation rentals offer extras like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for small groups.