Holiday Rentals in Dukes County

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Top Cities in Dukes County

Holiday RentalsHoliday Rentals

Vineyard Haven

Vineyard Haven

Featured Holiday Rentals in Dukes County

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, (30)
"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.
Interior

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

9.4 out of 10, Exceptional, (89)
"Close to buses, restaurants and ferries. 10/10, we would stay again."
The price is €438
includes taxes & fees
1 Oct - 2 Oct
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
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 €485
includes taxes & fees
4 Oct - 5 Oct
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
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
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
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
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
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
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!
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 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
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
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, (1)
"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
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)
"This home was absolutely beautiful. In a great location to get anywhere in the island. The host was extremely helpful when needed. I would one hundred percent recommend this place to anybody! "
CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS
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)
"This place is perfect, My girlfriend and I stayed there for Memorial Day weekend. It’s a quiet little cottage nestled in the wood we loved the privacy and getting away from the hustle and bustle of Oak bluffs at night. I’ve read some other reviews saying that the electricity doesn’t work but it worked for us the whole time. I personally plan on staying there again"
Nana's Backyard Treehouse with deck, electric/gas grills, kitchenette
Tranquil 5 BR House, Heated Saltwater Pool Near Downtown Edgartown
Outdoor pool, a heated pool

Tranquil 5 BR House, Heated Saltwater Pool Near Downtown Edgartown

9.4 out of 10, Exceptional, (11)
"House was in a great location for easy access to Edgartown. Lots of room in the house."
Tranquil 5 BR House, Heated Saltwater Pool Near Downtown Edgartown
Walking-distance to town, shops, restaurants & ferry!
Outdoor dining

Walking-distance to town, shops, restaurants & ferry!

10.0 out of 10, Exceptional, (22)
"I rented this for my staff, and they said it was the best place they have stayed on Martha's Vineyard."
Walking-distance to town, shops, restaurants & ferry!
Contemporary cottage with outdoor shower infrared sauna 6 Min drive to the beach
Terrace/patio

Contemporary cottage with outdoor shower infrared sauna 6 Min drive to the beach

9.0 out of 10, Wonderful, (2)
"Great house with enjoyable blend of spaciousness and cozy appeal. Kitchen was well appointed and great overall aesthetic, layout - roomy for 5. Upstairs suite very open and lots of windows in house. 5 min drive to BREATHTAKING reservation on beach ($20 to park for non members and well worth it), peaceful Japanese gardens nearby too. There's a super cute 500ft ferry ride ($35 round trip) to get to and from this location so plan for food accordingly!"
Contemporary cottage with outdoor shower infrared sauna 6 Min drive to the beach
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

Morgan Hotel

Morgan Hotel

10/10 Excellent
"It was good just no staff. "
James 2-night trip
Posted 4 days ago
Morgan Hotel

Find out more about Dukes County

Find out more about Dukes County

Holiday Homes in Dukes County

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