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Holiday rentals in Oak Bluffs, MA

Find deals on 362 holiday rentals in Oak Bluffs, MA

Oak Bluffs, MA, United States
29 Jun — 30 Jun2

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Top rentals in Oak Bluffs

Find the perfect holiday rental for your stay in Oak Bluffs
Price
£262
£1,607
Review Score
0+
6+
7+
8+
9+

Hostels and cheap hotels in Oak Bluffs

These hotels and hostels usually make for a cheap way to stay in Oak Bluffs
Coastal home with outdoor shower, grill, fireplace, central AC, & W/D Photo

Coastal home with outdoor shower, grill, fireplace, central AC, & W/D

Oak Bluffs, MA, United States

9.3
Cozy Vineyard Haven Cottage Less Than 1 Mi to Beach! Photo

Cozy Vineyard Haven Cottage Less Than 1 Mi to Beach!

Vineyard Haven, MA, United States

Quiet/ Wooded/ Walk to town: Shared home w/ 1 other guest room. Photo

Quiet/ Wooded/ Walk to town: Shared home w/ 1 other guest room.

Vineyard Haven, MA, United States

Charming studio with pool & tennis courts - close to beaches & golf

Oak Bluffs, MA, United States

Make Lasting Memories In This Adorable Vineyard Cottage! Photo

Make Lasting Memories In This Adorable Vineyard Cottage!

Oak Bluffs, MA, United States

9.9

Dog-friendly studio condo with pool & tennis - close to beaches & golf

Oak Bluffs, MA, United States

Get the best value holiday rental in Oak Bluffs

These Oak Bluffs holiday rentals have the best prices for their ratings
Coastal home with outdoor shower, grill, fireplace, central AC, & W/D Photo

Coastal home with outdoor shower, grill, fireplace, central AC, & W/D

Oak Bluffs, MA, United States

9.3
Brewster House Photo

Brewster House

Oak Bluffs, MA, United States

9.5
Make Lasting Memories In This Adorable Vineyard Cottage! Photo

Make Lasting Memories In This Adorable Vineyard Cottage!

Oak Bluffs, MA, United States

9.9
The Pinkletink Photo

The Pinkletink

Oak Bluffs, MA, United States

9.3
In-Town Certified National Historic Oak Bluffs Property - Photo

In-Town Certified National Historic Oak Bluffs Property -

Oak Bluffs, MA, United States

10.0
Marthas Vineyard Apt about 1 Mile to Inkwell Beach! Photo

Marthas Vineyard Apt about 1 Mile to Inkwell Beach!

Oak Bluffs, MA, United States

9.1

momondo's favourite holiday rentals in Oak Bluffs

Learn more about these user-preferred holiday rentals in Oak Bluffs
Lakefront Cottage with a Deck, Free WiFi, Gas Grill - Close to Ferries & Beaches Photo

Lakefront Cottage with a Deck, Free WiFi, Gas Grill - Close to Ferries & Beaches

Oak Bluffs, MA, United States

£368

Island Getaway

Oak Bluffs, MA, United States

3.5
£295
The Island Collection MV: Charming Cottage Located In Heart Of Oak Bluffs Photo

The Island Collection MV: Charming Cottage Located In Heart Of Oak Bluffs

Oak Bluffs, MA, United States

£646
The Island Collection MV: Enjoy This 1850s Victorian Home With Ocean Views! Photo

The Island Collection MV: Enjoy This 1850s Victorian Home With Ocean Views!

Oak Bluffs, MA, United States

£1,990
Make Lasting Memories In This Adorable Vineyard Cottage! Photo

Make Lasting Memories In This Adorable Vineyard Cottage!

Oak Bluffs, MA, United States

9.9
£188
Martha's Vineyard 3br, Pets Ok, 10 Min Walk To Beach Or Shops! Photo

Martha's Vineyard 3br, Pets Ok, 10 Min Walk To Beach Or Shops!

Edgartown, MA, United States

£553
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2025! Photo

Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2025!

Oak Bluffs, MA, United States

£1,154
Oak Bluffs Cottage - A Short Walk to the Beach! Photo

Oak Bluffs Cottage - A Short Walk to the Beach!

Oak Bluffs, MA, United States

£413
Beautiful 3 bedroom 2 bath Home / Close to Town & Beach Photo

Beautiful 3 bedroom 2 bath Home / Close to Town & Beach

Oak Bluffs, MA, United States

£569
Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts Photo

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

Oak Bluffs, MA, United States

£305
Spectacular Martha's Vineyard Island Home! Photo

Spectacular Martha's Vineyard Island Home!

Oak Bluffs, MA, United States

£479
Art Filled Beach Cottage In The Private Waterfront Community Of Waterview Farms! Photo

Art Filled Beach Cottage In The Private Waterfront Community Of Waterview Farms!

Oak Bluffs, MA, United States

£608
Close to town, beautifully updated Photo

Close to town, beautifully updated

Oak Bluffs, MA, United States

£796
Delilah & Joseph Pierce House Photo

Delilah & Joseph Pierce House

Oak Bluffs, MA, United States

£414
Modern 4 Bed/3.5 Bath Farmhouse, Private Heated Pool And Ac On Bike Path Photo

Modern 4 Bed/3.5 Bath Farmhouse, Private Heated Pool And Ac On Bike Path

Oak Bluffs, MA, United States

9.9
£1,152
Beautiful Custom Built House With A Pool And Hot Tub!!! Photo

Beautiful Custom Built House With A Pool And Hot Tub!!!

Oak Bluffs, MA, United States

£2,448
Peaceful Oak Bluffs Home Photo

Peaceful Oak Bluffs Home

Oak Bluffs, MA, United States

£450

Perfect for Family, Friends, or a Romantic Getaway - Newly Renovated!

Oak Bluffs, MA, United States

9.8
£261
Historic Oak Bluffs home, short walk to town, beach, and harbor. Photo

Historic Oak Bluffs home, short walk to town, beach, and harbor.

Oak Bluffs, MA, United States

£349
Charming Historic Island Home--Weekly Rental-- Oak Bluffs Photo

Charming Historic Island Home--Weekly Rental-- Oak Bluffs

Oak Bluffs, MA, United States

£486

Useful insights on Oak Bluffs holiday rentals

Get a quick overview on price and accommodation trends for your visit in Oak Bluffs

Lowest Holiday Rental Price

£188
The cheapest price for a room in Oak Bluffs found in the last 7 days is £188/night. This rate is available with Make Lasting Memories In This Adorable Vineyard Cottage!.

When to book a holiday rental in Oak Bluffs

Check out the information below to find the best deal on a holiday rental in Oak Bluffs
Low seasonSeptembercheapest month to stay
High seasonOctobermost expensive time to stay
45%expected price decrease
48%expected price increase

Price

£276 - £980

Cheapest day of weekWednesdayis the cheapest day of the week to book
Highest day of weekTuesdayis the most expensive day of the week to book
£334
£2,764

Information about staying in Oak Bluffs

Read these important travel tips before booking a holiday rental in Oak Bluffs

When is the best time to book a holiday rental in Oak Bluffs?

The cheapest month to rent a holiday apartment in Oak Bluffs is usually September. The cost of your apartment or rental property can be around 46% cheaper in September vs. the high season.

How many operators does momondo search for hotels in Oak Bluffs?

As of June 2025, there are 384 operators available to choose from for hotels in Oak Bluffs.

When did momondo last update prices for hotels in Oak Bluffs?

Prices for hotels in Oak Bluffs were last updated today.

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