A row of colorful, historic houses with a central path.

Holiday Homes in Oak Bluffs

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Oak Bluffs holiday homes

Terrace/patio

Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is €1,469
includes taxes & fees
3 Aug - 4 Aug
Walk to Beach! Oak Bluffs Home & Studio
TV, fireplace, books

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.4 out of 10, Exceptional, (6 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 €1,139
includes taxes & fees
30 Jul - 31 Jul
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Exterior

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Oak Bluffs
9.8 out of 10, Exceptional, (6 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is €1,819
includes taxes & fees
26 Jul - 27 Jul
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Interior

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (10 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 €1,959
includes taxes & fees
21 Jul - 22 Jul
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Exterior

Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"I can’t say enough about this beautiful property. pictures don’t do any justice for this piece of heaven. The flowers were everywhere , it’s so apparent that the property owners take such pride in this beautiful property. The place was spotless when we walked in the door. We met the owners on arrival , they surprised us with a beautiful ballon to celebrate my 50th birthday. My family enjoyed the pool and the fun Tiki. The outdoor fireplace was inviting after the sun went down. I was a little...
United States
Miriam D.
The price is €3,574
includes taxes & fees
23 Jul - 24 Jul
Beautiful Estate with salt water pool & pond with kayaks
Property grounds

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.8 out of 10, (9 reviews)
"This house was perfect. Super cute interior, well outfitted beds, plenty of space for our large family (2 adults, 4 kids, 1 small dog) - bonus points for the big laundry machines. Extra points for the super helpful and responsive host who went out of his way for us - even when I was messaging late at night on a Saturday after my daughter took a fall in Edgartown and had to be transported to Vineyard Hospital by ambulance. We will definitely rent this house again. Highly recommend!! "
United States
Nicole L.
The price is €886
includes taxes & fees
24 Jul - 25 Jul
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Dining

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely incredible stay! The host is so kind and helpful. House was very clean. Truly everything you need inside for cooking and beach fun! PERFECT location really centrally located to both edgartown and oak bluffs. Located in a quiet neighborhood near Felix Neck with lots of walking trails, which was very nice! Could not recommend this place more!"
United States
Katelyn W.
The price is €1,260
includes taxes & fees
19 Jul - 20 Jul
4-bedroom house in lovely Edgartown..Centrally located
Pool

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Fairhaven
9.6 out of 10, Exceptional, (35 reviews)
"We were looking for a weekend away from home, and we're lucky to find this place available. We got great recommendations for places to eat nearby, and were able to enjoy the area. We'd stay here again!"
United States
Zachary S.
The price is €444
includes taxes & fees
29 Jul - 30 Jul
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Dining

5 Mi to Beach: Cape Cod Getaway w/ Grill

5 Mi to Beach: Cape Cod Getaway w/ Grill
Sandwich
9.6 out of 10, Exceptional, (37 reviews)
"Great location & comfortable house for exploring Cape Cod & surrounding area"
United States
Linda
The price is €532
includes taxes & fees
20 Jul - 21 Jul
5 Mi to Beach: Cape Cod Getaway w/ Grill
Terrace/patio

Cozy Cottage walk to Menauhant Beach

Cozy Cottage walk to Menauhant Beach
East Falmouth
8.6 out of 10, Excellent, (7 reviews)
"It was a great weekend spot. Had everything we needed, nicely decorated, and in a great and private location"
United States
Grace P.
Cozy Cottage walk to Menauhant Beach
Property grounds

Chappy - Family Beach House

Chappy - Family Beach House
Edgartown
9.8 out of 10, Exceptional, (16 reviews)
"Sun-filled, comfortable, and perfectly located!"
United States
Carmin R.
Chappy - Family Beach House
Smart TV, fireplace

Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants

Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants
Barnstable
10.0 out of 10, Exceptional, (5 reviews)
"We had a great stay at the property, which was an ideal location - 5 minutes to the beach, playground, restaurants, etc. The fenced in yard made it very easy when having young children. The owner was very accommodating. I would recommended to future families. "
United States
Lauren G.
Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants
Property grounds

Charming 3 bed room with magnificent views & large deck

Charming 3 bed room with magnificent views & large deck
Barnstable
8.8 out of 10, Excellent, (6 reviews)
"We had a great stay in Hyannis! The location is great for catching a ferry to Nantucket or the vineyard, and Main Street is within walking distance. The backyard is also very peaceful for a cup of coffee in the morning! "
United States
Meghan H.
The price is €582
includes taxes & fees
13 Aug - 14 Aug
Charming 3 bed room with magnificent views & large deck
Fridge, microwave, oven, stovetop

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

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth
Falmouth
9.4 out of 10, Exceptional, (16 reviews)
"Really beautiful place with a lot of space and a very helpful host"
United States
Gokul K.
The price is €1,034
includes taxes & fees
22 Jul - 23 Jul
Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth
Coffee/tea maker, fridge, microwave, oven

Entire Hyannis Home - Near Downtown & Beaches

Entire Hyannis Home - Near Downtown & Beaches
Barnstable
10.0 out of 10, Exceptional, (2 reviews)
"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...
United States
Bethany P.
Entire Hyannis Home - Near Downtown & Beaches
Coffee/tea maker, fridge, microwave, oven

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, (33 reviews)
"It was a great stay and clean home. Recommend people to stay here"
United States
Charbel T.
The price is €1,180
includes taxes & fees
19 Jul - 20 Jul
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!
Interior

Backyard Retreat / 5 Min > Beach & Main St

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is €772
includes taxes & fees
20 Jul - 21 Jul
Backyard Retreat / 5 Min > Beach & Main St
Outdoor dining

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
7.0 out of 10, Good, (2 reviews)
"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 €1,170
includes taxes & fees
21 Jul - 22 Jul
Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !
Coffee/tea maker, fridge, microwave, oven

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, (7 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 €1,158
includes taxes & fees
19 Jul - 20 Jul
Spacious Lake House for Large Groups w Private Acre+ short path to Lake
Property grounds

New 4 BR house near center and beaches with bikes

New 4 BR house near center and beaches with bikes
Katama
10.0 out of 10, Exceptional, (7 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is €1,847
includes taxes & fees
30 Jul - 31 Jul
New 4 BR house near center and beaches with bikes
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

Sea Crest Beach Resort

Sea Crest Beach Resort

10/10 Excellent
"Great location, clean rooms and friendly staff. We try to go every summer."
Gina 1-night trip
Posted 9 hours ago
Sea Crest Beach Resort

Find out more about Oak Bluffs

Oak Bluffs Holiday Homes information

Number of reviews
173
Accommodation
1373 Holiday Homes
Lowest Price
€426
Highest Price
€3,574