A coastal cliff with a sandy beach and the ocean.

Aquinnah Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Aquinnah holiday rentals

A two-story house with a swimming pool, a covered patio, and a fenced backyard.

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 HK$2,505
HK$3,771 total
includes taxes & fees
13 Sept - 14 Sept
Cozy efficiency apartment/heated pool
A spacious living area with a high ceiling, a dining table, and a kitchen area.

2. 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 HK$2,470
HK$6,657 total
includes taxes & fees
18 Sept - 19 Sept
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A view through a window with a wooden frame, overlooking a garden with various plants and a body of water in the background.

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 HK$2,353
HK$4,204 total
includes taxes & fees
12 Oct - 13 Oct
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
A modern kitchen with white cabinets, a central island with blue drawers, and stainless steel appliances.

4. Brand New Guest house

Brand New Guest house
Oak Bluffs
10.0 out of 10, Exceptional, (7 reviews)
"This is a new, beautiful and tastefully decorated 2 bedroom one bathroom house with a really nice big yard. Owner was very responsive and We had everything we needed for an enjoyable stay!"
United States
Elizabeth O.
The price is HK$2,823
HK$7,507 total
includes taxes & fees
1 Oct - 2 Oct
Brand New Guest house
A living room with a flat-screen TV on a stand, a black leather chair, and a sofa. There are two windows with curtains, one of which offers a view of the sea.

5. 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, (95 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
The price is HK$2,353
HK$4,020 total
includes taxes & fees
20 Sept - 21 Sept
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
A circular stone patio with Adirondack chairs and a small table in a forested area.

6. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.6 out of 10, (11 reviews)
"We had a perfect pre-/off-season stay with plenty of sleeping space. The location is fantastic—right between Vineyard Haven and Edgartown—making it easy to bike to both, plus there’s a beach across the street. The WiFi wasn’t working when we first arrived, but the owner was incredibly responsive and went above and beyond to fix it quickly. We’ll definitely be back!"
United States
Bethann N.
The price is HK$2,627
HK$5,799 total
includes taxes & fees
5 Oct - 6 Oct
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
A spacious living area with a fireplace, a kitchen with bar stools, and a dining area with a table and chairs.

7. 4 Mi to Bristol Beach! Coastal Retreat w/ Pond

4 Mi to Bristol Beach! Coastal Retreat w/ Pond
East Falmouth
9.4 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay at this charming New England home. The house was spotless, beautifully maintained, and full of character. It had all the comforts we needed, inviting spaces to relax in after exploring the area. The location was perfect—close to local shops, scenic spots, and great dining. Our host was friendly, responsive, and made us feel right at home. We honestly couldn’t have asked for a better experience, and we look forward to returning."
United States
Shaun G.
The price is HK$1,035
HK$4,954 total
includes taxes & fees
5 Oct - 6 Oct
4 Mi to Bristol Beach! Coastal Retreat w/ Pond
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

8. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is HK$3,129
HK$6,202 total
includes taxes & fees
4 Oct - 5 Oct
Charming Vacation Home in Oak Bluffs.
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

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

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
8.4 out of 10, Very good, (10 reviews)
"Very good experience Very clean owner very helpful My second time here"
United States
Diana
The price is HK$2,580
HK$4,914 total
includes taxes & fees
13 Sept - 14 Sept
Walk to Beach & Lighthouse: Oak Bluffs Studio!

10. 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 HK$2,470
HK$3,924 total
includes taxes & fees
15 Sept - 16 Sept
Charming cottage overlooking the bay in Padanaram Village.
A wooden dining table with a lace tablecloth, surrounded by wooden chairs. A potted plant is on the table.

11. Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA

Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA
Dartmouth
10.0 out of 10, Exceptional, (1 review)
"Great location. Near ButtonWood Park. Quiet neighborhood. Enjoyed my stay."
United States
richard m.
The price is HK$925
HK$2,399 total
includes taxes & fees
25 Sept - 26 Sept
Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA
A residential area with a well-maintained lawn, a stone retaining wall, and a two-story house with a blue door.

12. 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 HK$4,156
HK$11,457 total
includes taxes & fees
24 Sept - 25 Sept
New 4 BR house near center and beaches with bikes
A spacious living area with a fireplace, a kitchen with bar stools, and a dining area with a table and chairs.

13. 4 Mi to Bristol Beach! Coastal Retreat w/ Pond

4 Mi to Bristol Beach! Coastal Retreat w/ Pond
3.0 star property
East Falmouth
The price is HK$1,372
HK$4,864 total
includes taxes & fees
5 Oct - 6 Oct
4 Mi to Bristol Beach! Coastal Retreat w/ Pond
A cozy living room with a wooden ceiling, a stone fireplace, a leather sofa, and a dining area with a table and chairs.

14. < 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
Oak Bluffs
7.4 out of 10, Good, (3 reviews)
"House was neat architectural wise and family history of home ownership was very cool. However, listing noted there was a washer/dryer and there was not. House also noted that there was a fire pit and it was rusted through. Screen door handles were broken, windows need repair, and house has animals living in the downstairs bathroom wall. House needs updates to charge what was being charged a night. In addition, there was a Nor’easter that hit the island and we attempted to contact the host to let...
United States
Kate K.
The price is HK$2,572
HK$6,281 total
includes taxes & fees
13 Sept - 14 Sept
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
A water park with a large central pool, multiple slides, and a variety of play structures.

15. Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Fairhaven
9.6 out of 10, Exceptional, (40 reviews)
"The most perfect spot! Our host and the neighbors were so nice and gave us great tips! Would definitely stay again"
United States
Jainessa
The price is HK$1,764
HK$3,959 total
includes taxes & fees
30 Sept - 1 Oct
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
A deck with a fire pit, outdoor seating, and a blue umbrella.

16. 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 HK$1,502
HK$5,954 total
includes taxes & fees
13 Sept - 14 Sept
Cozy Cottage walk to Menauhant Beach
A bedroom with a bed, a dresser, a sofa, and a painting on the wall.

17. Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
10.0 out of 10, Exceptional, (2 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 HK$1,129
HK$1,723 total
includes taxes & fees
22 Sept - 23 Sept
Charming studio in tranquil Falmouth with AC
A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

18. 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, (8 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is HK$3,121
HK$10,721 total
includes taxes & fees
1 Oct - 2 Oct
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A modern living room with a grey sofa, a coffee table, and a fireplace.

19. LUX on Main | Downtown | Parking | Sleeps 6, #203

LUX on Main | Downtown | Parking | Sleeps 6, #203
Falmouth
10.0 out of 10, Exceptional, (6 reviews)
The price is HK$2,261
HK$6,662 total
includes taxes & fees
13 Sept - 14 Sept
LUX on Main | Downtown | Parking | Sleeps 6, #203
A modern kitchen with white cabinetry, a central island with stools, a blue sofa, and a round coffee table.

20. Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Tisbury
10.0 out of 10, Exceptional, (42 reviews)
"Great place, awesome location!"
United States
Connor B.
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
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

Iris Hotel Cape Cod

Iris Hotel Cape Cod

10/10 Excellent
"The staff from the front desk to the cafe were polite, helpful and very welcoming. Our room was truly handicap accessible, with a shower seat over the tub, adjustable shower and amenities within easy reach. Breakfast was beyond expectations. We stayed here before and after our excursion to MV and we would highly recommend to anyone traveling in Cape Cod or going to Martha’s Vineyard or Nantucket."
Howie 1-night trip
Posted 13 hours ago
Iris Hotel Cape Cod

Find out more about Aquinnah

Search for holiday rentals in Aquinnah on Expedia! You can easily find your home rentals, villas, holiday apartments in Aquinnah using one of the methods below:

  • View our selection of featured holiday rentals in Aquinnah
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  • Enter your travel dates to view the best deals on holiday rentals in Aquinnah while they last

Look no further and take a look at our great range of rental properties in Aquinnah!

Frequently asked questions

Are there holiday rentals in Aquinnah?

Yes, there are holiday rentals close to the most popular sights in Aquinnah, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Aquinnah has to offer?

Gorgeous Spacious Victorian Cape Cod Beach View Retreat: This holiday home rental outside of Aquinnah is located near the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Aquinnah?

With 31 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Aquinnah?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Aquinnah. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.