A coastal town with houses, a lighthouse, and a rocky shoreline.

East Chop Holiday Rentals

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Our top choices for East Chop holiday rentals

1. 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 NZ$2,258
includes taxes & fees
1 Oct - 2 Oct
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

2. 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 NZ$902
includes taxes & fees
10 Sept - 11 Sept
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

3. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (367 reviews)
"Overall, very good. Pool and beach area were not the most convenient to access. Short drive required."
United States
Grayson
The price is NZ$418
includes taxes & fees
8 Sept - 9 Sept
The Club at New Seabury

4. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
9.8 out of 10, Exceptional, (30 reviews)
"Lovely and all brand new accommodation's that are clean and comfy! A quiet location too! "
United States
Nancy K.
The price is NZ$765
includes taxes & fees
7 Sept - 8 Sept
Brand new! Lovely apartment-Vineyard Haven

5. Lovely two bedroom apartment with indoor fireplace

Lovely two bedroom apartment with indoor fireplace
Oak Bluffs
10.0 out of 10, Exceptional, (8 reviews)
"Great stay, flexible and responsive host. Difficult location, however, as it was not centrally located or easy to access transportation, etc."
United States
Aviva M.
The price is NZ$1,248
includes taxes & fees
7 Sept - 8 Sept
Lovely two bedroom apartment with indoor fireplace

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

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
8.4 out of 10, Very good, (9 reviews)
"Very good experience Very clean owner very helpful My second time here"
United States
Diana
The price is NZ$1,020
includes taxes & fees
13 Sept - 14 Sept
Walk to Beach & Lighthouse: Oak Bluffs Studio!

7. 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)
"Danny was a great host. Unit clean. Walking distance to everything"
United States
Alvin
The price is NZ$872
includes taxes & fees
1 Oct - 2 Oct
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

8. New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (89 reviews)
"Great condo, great location. Fully equipped kitchen and awesome patio. "
United States
Jeff V.
The price is NZ$557
includes taxes & fees
7 Sept - 8 Sept
New Seabury Cape Condo + Pool & Beach Escape

9. < 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 NZ$1,305
includes taxes & fees
13 Sept - 14 Sept
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

10. 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 NZ$1,191
includes taxes & fees
7 Sept - 8 Sept
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

11. 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, (8 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 NZ$893
includes taxes & fees
20 Sept - 21 Sept
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

12. Brand New Guest house

Brand New Guest house
Oak Bluffs
10.0 out of 10, Exceptional, (6 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 NZ$1,586
includes taxes & fees
1 Oct - 2 Oct
Brand New Guest house

13. Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!

Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!
Oak Bluffs
9.8 out of 10, Exceptional, (60 reviews)
"We had the best girls weekend here! The space was perfect size for us. Great spaces for sitting and chatting, both inside and on the balcony. The location was perfect, right across from the ocean waves and shells on the beach. Walking distance to town and easy access to biking. It had everything we needed."
United States
Rachael C.
The price is NZ$1,498
includes taxes & fees
24 Sept - 25 Sept
Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!

14. 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 NZ$1,396
includes taxes & fees
17 Sept - 18 Sept
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

15. 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, (41 reviews)
"Great place, awesome location!"
United States
Connor B.
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

16. WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (54 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
WATERFRONT Downtown Cottage w/ Beach

17. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is NZ$1,373
includes taxes & fees
27 Sept - 28 Sept
Charming Vacation Home in Oak Bluffs.

18. 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 NZ$1,266
includes taxes & fees
8 Sept - 9 Sept
Cozy Cottage walk to Menauhant Beach

19. Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
Seconsett Island
10.0 out of 10, Exceptional, (42 reviews)
"Great stay!"
United States
Kian S.
The price is NZ$704
includes taxes & fees
17 Sept - 18 Sept
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

20. 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 NZ$1,043
includes taxes & fees
5 Oct - 6 Oct
4 Mi to Bristol Beach! Coastal Retreat w/ Pond
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 East Chop Hotel Reviews

Find out more about East Chop

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our East Chop holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up East Chop. 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 East Chop. Seeing all the best attractions is bound to make you fall in love with East Chop. Who knows, you may even be tempted to extend your 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 holiday 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 East Chop short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in East Chop?

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

What are some of the best holiday rentals that East Chop has to offer?

Gorgeous Spacious Victorian Cape Cod Beach View Retreat: This holiday home rental outside of East Chop 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 will I find in East Chop?

Expedia has 23 holiday rentals for your stay in East Chop.

What can I see and do in East Chop?

While exploring the area, visit family-friendly sights like Cape Cod Children's Museum, or get outside and enjoy nature at Oak Bluffs Town Beach. In the wider area, you’ll find East Chop Light and Oak Bluffs Harbor.

What are holiday rentals like in East Chop?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in East Chop. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips or small group gatherings.