Oak Bluffs Holiday Houses

Sunrise striking the houses at Oak Bluffs on Martha's Vineyard, MA.

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Our top choices for Oak Bluffs holiday homes

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Oak Bluffs

Karen M.

includes taxes & fees

2 June - 3 June

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Oak Bluffs

Swathanthra M.

includes taxes & fees

7 June - 8 June

Beautiful Estate with salt water pool & pond with kayaks

Oak Bluffs

includes taxes & fees

11 June - 12 June

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Barnstable

Kim

includes taxes & fees

2 June - 3 June

Trendy Great Pond Escape! HotTub Open! Sleeps 9!

Falmouth

Reed W.

includes taxes & fees

1 June - 2 June

4-bedroom house in lovely Edgartown..Centrally located

Edgartown

includes taxes & fees

1 June - 2 June

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

Falmouth

Gokul K.

includes taxes & fees

7 June - 8 June

2 Mi to Dowses Beach! Couples Haven in Osterville

Osterville

includes taxes & fees

14 June - 15 June

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Falmouth

Linda W.

includes taxes & fees

21 June - 22 June

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

Barnstable

"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...

Madilynn B.

includes taxes & fees

11 June - 12 June

Bike to Beach: Centerville Home w/ Deck!

Centerville

Jeanne S.

includes taxes & fees

7 June - 8 June

Hyannis Hideaway in Cape Cod

Barnstable

Hunter W.

includes taxes & fees

7 June - 8 June

Charming 3 bed room with magnificent views & large deck

Barnstable

Rose T.

includes taxes & fees

16 June - 17 June

Entire Hyannis Home - Near Downtown & Beaches

Barnstable

"We had a fantastic stay! The property was extremely clean from top to bottom, which immediately made us feel comfortable settling in. The beds and linens were incredibly comfortable and we all slept great.The location was also a huge plus. It is close to great restaurants, local events and plenty to do in the area, making it easy to get around and enjoy everything nearby.The host was extremely communicative and responsive, which made the whole experience smooth and stress free from booking...

Bethany P.

4-bedroom waterfront house in E. Falmouth with WiFi, AC, Hot Tub, Private Beach

Falmouth

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

Barnstable

Ally D.

includes taxes & fees

7 June - 8 June

Spring Escape in Hatchville – Sleeps 6 + Dogs!

Falmouth

Lynn S.

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

Barnstable

Charbel T.

includes taxes & fees

1 June - 2 June

Booking Summer 2026 Cape Escape! Modern Tranquil Cape home close to town beaches

Falmouth

Laura K.

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

Falmouth

Gail B.

includes taxes & fees

7 June - 8 June

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Top Oak Bluffs Hotel Reviews

Hyannis Plaza Hotel

10/10 Excellent

"Todo muy bien"

Sea Crest Beach Resort

2/10 Terrible

"Check in was chaotic. I’m the staff called the room phone at 11:05pm stating they needed me to come back to the front desk for additional information. I asked the manager why they would call and wake me and my young child up past 11 pm for a reservation that had been paid for weeks in advance. They don’t tell you there are additional fees to use the beach / pool. The hallway smelled like cigarettes and many guests had barking dogs. Certainly not worth the price. The staff was inattentive, unfriendly and like common courtesy."

Vineyard Harbor Motel - Private Beach

10/10 Excellent

"We made a very last minute reservation when our ferry was canceled due to weather. The person at the desk moved us to the first floor because we had a stroller and got us a pack and play and was just super helpful during a very stressful time. Our room had a full kitchen with full sized fridge, oven, microwave, and was overall clean and exactly what we needed when traveling with a baby. We didn’t get to enjoy the beach because of the weather but it’s super close to the ferry - you can actually see the boat - and to some nice restaurants and cafes. Exceeded expectations!"

Summercamp

10/10 Excellent

"Summercamp is walking distance to all the shops and restaurants in Oak Bluffs. It has a large front porch with oversized modern rocking chairs and a view of the lake. It is also a short walk to the ferry and the bus stop that takes you to Edgartown and Vineyard Haven. It was so easy to get around. The Property Manager, Kate and her entire crew had the best hospitality that we have had at any hotel. Everyone was so professional, pleasant and accommodating. It is not how something goes wrong but how the staff manages it: When we arrived, there was unexpected groundwork being done. When we returned from a walk, there was a front loader and a sewer truck working right outside our bedroom window. We asked to be moved to another room. The Manager, Kate, personally came to speak to us and explained how it was historical septic that had caused a sinkhole and it was all being removed but wouldn't impact our plumbing. However, she offered to move us to another room and credited us the difference. She also had champagne and treats waiting for us in the new room. (It was my sister's 60th birthday.) The work was completed the day we left. It was not something the staff could predict or prevent. However, the Manager, Kate took the time with us to ensure that we had a nice experience for our first time at Summercamp. We will be repeat guests! Thank you to Kate and her crew!"

Admiralty Inn & Suites - a Red Collection Hotel

10/10 Excellent

"Loved the property and the staff. The room was very clean, the bed was very comfortable, the TV had all the channels we needed. They key card gave us an issue with deactivation. If you put it next to your phone in your pocket, it deactivates. The breakfast was better than expected for a “continental” style of breakfast. Overall, we had a great experience and we will go back"

Find out more about Oak Bluffs

Oak Bluffs Holiday Homes information

Number of reviews	359
Accommodation	1286 Holiday Homes
Lowest Price	NZ$420
Highest Price	NZ$5,163

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Oak Bluffs holiday homes

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Beautiful Estate with salt water pool & pond with kayaks

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Trendy Great Pond Escape! HotTub Open! Sleeps 9!

4-bedroom house in lovely Edgartown..Centrally located

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

2 Mi to Dowses Beach! Couples Haven in Osterville

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area