Dukes County Holiday Rentals

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Featured Dukes County Holiday Rentals

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 HK$2,335
HK$4,173 total
includes taxes & fees
1 Nov - 2 Nov
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 HK$2,102
HK$3,878 total
includes taxes & fees
8 Oct - 9 Oct
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 home was wonderful, such a treasure. Great for family and friends. Large kitchen provides ample room for entertaining, all the supplies you need. Hope to be able to go back."
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
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
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
Heart of VH, walk to ferry, shops & restaurants. Pool, AC & beach gear provided!
Outdoor pool

Heart of VH, walk to ferry, shops & restaurants. Pool, AC & beach gear provided!

9.8 out of 10, Exceptional, (25)
"We had a lovely time, everything was very clean and Matthew was very welcoming. Everything that we needed was right at hand!"
Heart of VH, walk to ferry, shops & restaurants. Pool, AC & beach gear provided!
Cozy cottage 3/4 mile from Oak Bluffs harbor
Exterior

Cozy cottage 3/4 mile from Oak Bluffs harbor

9.8 out of 10, Exceptional, (49)
"Stayed here with 3 friends as we were running the marathon. Better than the photos! So cute, everything was thoughtfully set up, we had anything we needed and having a washer dryer was a huge bonus! Flexible check in as well. Secluded, but easily walkable to many great places to eat and shop. Would 100% stay here again, highly recommend."
Cozy cottage 3/4 mile from Oak Bluffs harbor
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
2 bedrooms, iron/ironing board, WiFi, bed sheets

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

9.0 out of 10, Wonderful, (15)
"Had a lovely stay for a week in September with our dog! House is clean, well stocked and in a very private location. The house is perfect for a couple or small family. We could not have asked for a better stay! Highly recommend!"
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
New construction Edgartown home with AC, new furnishings, o/d shower, bike path.
Sun-loungers, beach towels

New construction Edgartown home with AC, new furnishings, o/d shower, bike path.

10.0 out of 10, Exceptional, (147)
"Really nice comfortable home. Very well outfitted. We loved the fireplace and Stephen was super accommodating to our ever changing plans. "
New construction Edgartown home with AC, new furnishings, o/d shower, bike path.
Spacious 5-bedroom secluded house in West Tisbury - Lambert Cove's Beach Pass
Property grounds

Spacious 5-bedroom secluded house in West Tisbury - Lambert Cove's Beach Pass

10.0 out of 10, Exceptional, (2)
"We had a wonderful stay at this house. We really enjoyed the location and beach pass to Lambert’s Cove. The host was response and friendly. The house was very cute and had plenty of space for all of us. "
Spacious 5-bedroom secluded house in West Tisbury - Lambert Cove's Beach Pass
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 HK$1,362
HK$5,181 total
includes taxes & fees
20 Oct - 21 Oct
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS
Beach nearby, sun-loungers, beach towels

CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS

9.6 out of 10, Exceptional, (31)
"We had such a wonderful stay. Thank you."
CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS
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 HK$4,280
HK$9,432 total
includes taxes & fees
20 Oct - 21 Oct
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
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 Dukes County Hotel Reviews

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

10/10 Excellent
"Rooms were clean and comfortable a quick walk to the center of town PLUS there was a cute little beach!"
Michelle 1-night trip
Posted 2 days ago
Vineyard Harbor Motel - Private Beach