Menemsha Vacation Rentals

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Oct 1 - Oct 2
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Oct 2 - Oct 3
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Oct 3 - Oct 5
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Oct 10 - Oct 12

Vacation Rentals in Menemsha

InnSeason Resorts Captain's Quarters
On the beach, white sand

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (181)
"Great location and helpful staff"
InnSeason Resorts Captain's Quarters
Coastal chic meets French Provençal in this newly renovated oceanfront home.
5 bedrooms, desk, iron/ironing board, travel crib

Coastal chic meets French Provençal in this newly renovated oceanfront home.

10.0 out of 10, Exceptional, (85)
"Great stay! "
The price is ￥92,450
￥197,229 total
includes taxes & fees
Oct 27 - Oct 28
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Exterior

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

6.4 out of 10, (31)
"The weather was perfect and our crew made the best of our trip."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Smart TV

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

9.4 out of 10, Exceptional, (88)
"The location of this property cannot be beat! Our second time staying here."
The price is ￥44,376
￥79,309 total
includes taxes & fees
Nov 1 - Nov 2
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts
Property grounds

Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts

9.8 out of 10, Exceptional, (78)
"Central property with all essentials!"
Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Interior

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

9.4 out of 10, Exceptional, (91)
"Close to buses, restaurants and ferries. 10/10, we would stay again."
The price is ￥39,938
￥73,690 total
includes taxes & fees
Oct 8 - Oct 9
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
Exterior

Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

10.0 out of 10, Exceptional, (64)
"The house was well stocked and had everything you could need. "
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
Terrace/patio

Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

8.8 out of 10, Excellent, (33)
"The peaceful woodland setting is just beautiful! Enjoyed a quiet stay in this spacious one bedroom house. The porch wraps around entire house and gave our morning coffee and breakfast a very special vacation feel."
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
Cozy Beach Cottage
Beach nearby, sun loungers, beach towels

Cozy Beach Cottage

10.0 out of 10, Exceptional, (53)
"This was the perfect property for our visit to Martha’s Vineyard. The owners were so responsive and gave us a seamless experience. I would definitely stay at the Cozy Cottage again! "
Cozy Beach Cottage
The Costal Corner - Martha's Vineyard
Microwave, oven, stovetop, dishwasher

The Costal Corner - Martha's Vineyard

2.0 star property
10.0 out of 10, Exceptional, (3)
"This property was great for our golf trip. The 3 bedrooms were exceptional "
The Costal Corner - Martha's Vineyard
Beachside Village Resort
Seasonal outdoor pool

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (99)
"Great location! Nice property! "
Beachside Village Resort
By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound
Property grounds

By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound

9.8 out of 10, Exceptional, (23)
"We had a great week staying at this property. It's well maintained and had plenty of room for a family getaway to the Cape. Steps away from the beach, this property is well taken care of and had everything we needed for a comfortable stay. This would be our first choice for any future trips to the Cape."
By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound
Spacious colonial home close to town with AC, porches, & W/D
TV, DVD player, books

Spacious colonial home close to town with AC, porches, & W/D

10.0 out of 10, Exceptional, (5)
Spacious colonial home close to town with AC, porches, & W/D
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
Fridge, microwave, oven, stovetop

Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!

10.0 out of 10, Exceptional, (71)
"Large home with plenty of room for extended family. Located in quiet neighborhood close to Oak Bluffs, would highly recommend."
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
Spacious home in central location with beautiful patio, pool table, W/D, & AC
Exterior

Spacious home in central location with beautiful patio, pool table, W/D, & AC

2.0 star property
10.0 out of 10, Exceptional, (4)
"Absolutely loved our stay at this Oak Bluffs home! The location was perfect—just a 20-minute walk to downtown—and the house itself was warm, inviting, and beautifully laid out with an open-air feel. The kitchen was fully stocked, the beds were super comfortable, and the outdoor shower was a wonderful bonus. We felt completely relaxed and free during our stay. Can’t wait to come back next summer!"
Spacious home in central location with beautiful patio, pool table, W/D, & AC
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Terrace/patio

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

10.0 out of 10, Exceptional, (28)
"Perfect for my family of 4. Very walkable to everything Vineyard Haven. "
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Interior

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

10.0 out of 10, Exceptional, (7)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
The price is ￥81,356
￥179,272 total
includes taxes & fees
Oct 2 - Oct 3
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
TV, fireplace, books

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

9.0 out of 10, Wonderful, (2)
"The house was lovely. Very clean and orderly. Beautiful back porch that we enjoyed very much. The beds were very comfortable. Our only complaint was the Master bathroom needs some updating. The shower head desperately needs to be changed and the lighting is extremely poor. Also, only 1 half size mirror on the whole first floor. Other than that, it was perfect."
The price is ￥25,886
￥99,137 total
includes taxes & fees
Oct 28 - Oct 29
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
3 Bed 2 Bath - Fully Renovated SS Granite kitchen walk to beach Falmouth heights
Dining

3 Bed 2 Bath - Fully Renovated SS Granite kitchen walk to beach Falmouth heights

9.2 out of 10, Wonderful, (35)
"Everything was great "
3 Bed 2 Bath - Fully Renovated SS Granite kitchen walk to beach Falmouth heights
Nana's Backyard Treehouse with deck, electric/gas grills, kitchenette
Terrace/patio

Nana's Backyard Treehouse with deck, electric/gas grills, kitchenette

8.0 out of 10, Very Good, (15)
"Well maintained. Very quiet. No TV. Doubt if there is any air conditioning. "
Nana's Backyard Treehouse with deck, electric/gas grills, kitchenette
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 Menemsha Hotel Reviews

Faraway Martha's Vineyard

Faraway Martha's Vineyard

10/10 Excellent
"Perfect in every way. Beautiful decor, central location, smells wonderful "
Steven J. 2-night trip
Posted 17 hours ago
Faraway Martha's Vineyard

Find out more about Menemsha

Find out more about Menemsha

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

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Frequently asked questions

Are there vacation rentals in Menemsha?

Yes, we offer vacation rentals close to the most popular sights in Menemsha, or you can go with a more remote option if you're looking for relaxation.

What are some of the best vacation home rentals in Menemsha?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: This vacation home rental outside of Menemsha is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals will I find in Menemsha?

Expedia has 6 vacation rentals for your stay in Menemsha.

What’s there to see and do in Menemsha?

Explore the area and family-friendly sights such as Oak Bluffs Fishing Pier, or get out into nature at a spot like Menemsha Beach. In the larger area, you’ll find Gay Head Lighthouse and Aquinnah Cliffs.

What’s a vacation rental in Menemsha like?

A vacation rental is a private property you can stay in for short or long periods in Menemsha. Vacation rentals offer extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for family trips.