Holiday Homes in Oak Bluffs

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Our top choices for Oak Bluffs holiday homes

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
10.0 out of 10, Exceptional, (7 reviews)
"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."
United States
Swathanthra M.
The price is AU$1,650
includes taxes & fees
1 Mar - 2 Mar
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.4 out of 10, Exceptional, (3 reviews)
"This house was perfect for our getaway. Rebecca, the host, was extremely responsive and helpful during our trip. The house was as advertised. It was clean, well equipped, and the location was perfect as well "
United States
Louis R.
The price is AU$1,213
includes taxes & fees
1 Mar - 2 Mar
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Oak Bluffs - Quiet neighborhood

Oak Bluffs - Quiet neighborhood
Oak Bluffs
9.4 out of 10, Exceptional, (43 reviews)
"Perfectly situated!"
United States
Damani B.
The price is AU$930
includes taxes & fees
4 Mar - 5 Mar
Oak Bluffs - Quiet neighborhood

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (212 reviews)
"This beautiful well-appointed home was the perfect spot for a girlfriend’s getaway. Walkable to the shops and restaurants, nice big rooms for chats, and a great kitchen island to congregate around for breakfast. We loved our time here!"
United States
Annemarie G.
The price is AU$603
includes taxes & fees
3 Mar - 4 Mar
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!
Barnstable
10.0 out of 10, Exceptional, (31 reviews)
"It was a great stay and clean home. Recommend people to stay here"
United States
Charbel T.
The price is AU$1,332
includes taxes & fees
1 Mar - 2 Mar
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Tisbury
10.0 out of 10, Exceptional, (16 reviews)
"We had an amazing time at this beautiful home. Great, clean space to spend an evening visit with friends and family. Great location with easy access around the island. Would highly recommend! "
United States
Jennifer T.
The price is AU$1,478
includes taxes & fees
2 Mar - 3 Mar
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

Falmouth Oasis

Falmouth Oasis
Falmouth
The price is AU$678
includes taxes & fees
1 Mar - 2 Mar
Falmouth Oasis

Entire Hyannis Home - Near Downtown & Beaches with Parking Pass

Entire Hyannis Home - Near Downtown & Beaches with Parking Pass
Barnstable
The price is AU$657
includes taxes & fees
10 Mar - 11 Mar
Entire Hyannis Home - Near Downtown & Beaches with Parking Pass

Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
Barnstable
10.0 out of 10, Exceptional, (5 reviews)
"Very nice property in a quiet and convenient location. Private backyard with outdoor shower. Interior was completely updated with very nice furnishings and appliances. All in all a great home that we will definitely return to. "
United States
Jim C.
The price is AU$931
includes taxes & fees
1 Mar - 2 Mar
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !

Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !
Barnstable
10.0 out of 10, Exceptional, (1 review)
"My family and I thoroughly enjoyed our week long stay at the beautiful property. There were 12 of us and we were extremely comfortable, with plenty of space to gather and sleep. The property sits on a quiet pond, that was perfect for swimming and canoeing. We had our own little piece of paradise. There are canoes for use, several decks for lounging and was within a short distance to various shops and a grocery store just a few minutes away. The host was in constant contact with us, making sure...
United States
Madilynn B.
The price is AU$1,508
includes taxes & fees
1 Mar - 2 Mar
Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !

The Beach Estate, Panoramic Ocean Views, 5700 sqft

The Beach Estate, Panoramic Ocean Views, 5700 sqft
Mattapoisett
9.8 out of 10, Exceptional, (8 reviews)
"Great stay! Great property!"
United States
Liz A.
The Beach Estate, Panoramic Ocean Views, 5700 sqft

Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
New Seabury
10.0 out of 10, Exceptional, (8 reviews)
"Great place"
United States
Aaron Q.
The price is AU$1,564
includes taxes & fees
1 Mar - 2 Mar
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (25 reviews)
"Property was perfectly kept and very comfortable. "
United States
Steve D.
The price is AU$780
includes taxes & fees
30 Mar - 31 Mar
The Seashell Cove - Martha's Vineyard

Contemporary 4-bedroom ranch style home with AC in charming Falmouth, Cape Cod

Contemporary 4-bedroom ranch style home with AC in charming Falmouth, Cape Cod
Falmouth
The price is AU$1,007
includes taxes & fees
16 Mar - 17 Mar
Contemporary 4-bedroom ranch style home with AC in charming Falmouth, Cape Cod

Hyannis Hideaway in Cape Cod

Hyannis Hideaway in Cape Cod
Barnstable
10.0 out of 10, Exceptional, (2 reviews)
"Awesome private property, close to Main Street and Craigsville beach. My friends and I stay in Hyannis every 4th of July and this home was super accommodating for groups and close to everything. Great stay would recommend. "
United States
Hunter W.
The price is AU$835
includes taxes & fees
1 Mar - 2 Mar
Hyannis Hideaway in Cape Cod

Spacious Lake House for Large Groups w Private Acre+ short path to Lake

Spacious Lake House for Large Groups w Private Acre+ short path to Lake
Barnstable
8.0 out of 10, Very good, (5 reviews)
"Had a great stay here - the hosts were flexible with our early check in and made the whole trip a smooth process! "
United States
Ally D.
The price is AU$1,549
includes taxes & fees
1 Mar - 2 Mar
Spacious Lake House for Large Groups w Private Acre+ short path to Lake

Summer 2026 Perfection!

Summer 2026 Perfection!
Barnstable
The price is AU$725
includes taxes & fees
1 Mar - 2 Mar
Summer 2026 Perfection!

Sal's Place

Sal's Place
2.0 star property
Hyannis
The price is AU$812
includes taxes & fees
1 Mar - 2 Mar
Sal's Place

Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!

Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!
Edgartown
9.8 out of 10, Exceptional, (16 reviews)
"Overall great experience"
United States
Scott P.
The price is AU$1,445
includes taxes & fees
1 Mar - 2 Mar
Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!

Cape Cod Escape at Casa de Leo!

Cape Cod Escape at Casa de Leo!
Falmouth
The price is AU$2,110
includes taxes & fees
1 Mar - 2 Mar
Cape Cod Escape at Casa de Leo!
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 Oak Bluffs Hotel Reviews

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Oak Bluffs Holiday Homes information

Number of reviews
382
Accommodation
1300 Holiday Homes
Lowest Price
AU$603
Highest Price
AU$2,110