Holiday Homes in Oak Bluffs

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Oak Bluffs and around

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
TV, fireplace, books

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

9.0 out of 10, Wonderful, (2)
"The house was lovely. Very clean and orderly. Beautiful back porch that we enjoyed very much. The beds were very comfortable. Our only complaint was the Master bathroom needs some updating. The shower head desperately needs to be changed and the lighting is extremely poor. Also, only 1 half size mirror on the whole first floor. Other than that, it was perfect."
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Interior

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

10.0 out of 10, Exceptional, (7)
"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."
The price is €2,088
includes taxes & fees
1 Sept - 2 Sept
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Exterior detail

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

The price is €548
includes taxes & fees
1 Sept - 2 Sept
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Island Inn - 2 Bedroom & 2 Bath Townhouse - 50G - Oak Bluffs, MA
Beach

Island Inn - 2 Bedroom & 2 Bath Townhouse - 50G - Oak Bluffs, MA

10.0 out of 10, Exceptional, (1)
"Great location, clean, quiet, great amenities inside AND out, loved having special access to Nomans, we were VERY happy with our stay. Thank you for such an awesome option to enjoy MV and Island Life!"
The price is €1,014
includes taxes & fees
28 Aug - 29 Aug
Island Inn - 2 Bedroom & 2 Bath Townhouse - 50G - Oak Bluffs, MA
Island Inn - 2 Bedroom & 2 Bath Townhouse - 44G - Oak Bluffs, MA
Beach

Island Inn - 2 Bedroom & 2 Bath Townhouse - 44G - Oak Bluffs, MA

9.0 out of 10, Wonderful, (2)
"Great location. Very nice property. The unit was clean but dated in a few areas. Overall, it was perfect for 4 of us visiting for the wknd. "
The price is €1,076
includes taxes & fees
19 Aug - 20 Aug
Island Inn - 2 Bedroom & 2 Bath Townhouse - 44G - Oak Bluffs, MA
Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 43G - Dog-friendly - Oak Bluffs, MA
Beach

Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 43G - Dog-friendly - Oak Bluffs, MA

The price is €1,026
includes taxes & fees
24 Aug - 25 Aug
Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 43G - Dog-friendly - Oak Bluffs, MA
Island Inn - 2 Bedroom & 2 Bath Townhouse - 48G - Oak Bluffs, MA
Beach

Island Inn - 2 Bedroom & 2 Bath Townhouse - 48G - Oak Bluffs, MA

The price is €884
includes taxes & fees
2 Sept - 3 Sept
Island Inn - 2 Bedroom & 2 Bath Townhouse - 48G - Oak Bluffs, MA
Charming 3 bed room with magnificent views & large deck
Exterior

Charming 3 bed room with magnificent views & large deck

8.0 out of 10, Very good, (1)
". Great locations. Short walk to numerous restaurants and ferry. "
The price is €401
includes taxes & fees
9 Sept - 10 Sept
Charming 3 bed room with magnificent views & large deck
Remodeled historical Gosnold Cottage.300 yards to the beach.
Property grounds

Remodeled historical Gosnold Cottage.300 yards to the beach.

10.0 out of 10, Exceptional, (3)
"We had a great stay at this property! It was very clean and spacious for our family of 4. Veterans Beach was within walking distance. The shower was great and my 2 year old loved to run around the property l would definitely stay here again"
The price is €525
includes taxes & fees
7 Sept - 8 Sept
Remodeled historical Gosnold Cottage.300 yards to the beach.
Gosnold Manor 300 Yards To Veterans Park Beach, recently updated home.
Beach nearby, sun-loungers, beach towels

Gosnold Manor 300 Yards To Veterans Park Beach, recently updated home.

9.8 out of 10, Exceptional, (26)
"Great peaceful calming"
The price is €1,027
includes taxes & fees
27 Aug - 28 Aug
Gosnold Manor 300 Yards To Veterans Park Beach, recently updated home.
Beautiful Private Beach House
Smart TV

Beautiful Private Beach House

10.0 out of 10, Exceptional, (48)
"The property was lovely with amazing views and a comfortable atmosphere. The host was very responsive. It was a great long weekend retreat for a multi-generational family."
Beautiful Private Beach House
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Beach nearby

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

8.8 out of 10, Excellent, (5)
"Perfect to walk to the beach"
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
3-bedroom house in charming Barnstable with WiFi, AC,Walking distance to Main st
Exterior

3-bedroom house in charming Barnstable with WiFi, AC,Walking distance to Main st

3-bedroom house in charming Barnstable with WiFi, AC,Walking distance to Main st
The Sunshine Cape Family/DogFriendly GameRoom Outdoor Shower
Exterior detail

The Sunshine Cape Family/DogFriendly GameRoom Outdoor Shower

9.0 out of 10, Wonderful, (7)
"Great accommodations very clean."
The Sunshine Cape Family/DogFriendly GameRoom Outdoor Shower
Hyannis Hideaway in Cape Cod
Paper towels

Hyannis Hideaway in Cape Cod

10.0 out of 10, Exceptional, (2)
"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. "
The price is €620
includes taxes & fees
8 Sept - 9 Sept
Hyannis Hideaway in Cape Cod
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
Terrace/patio

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

10.0 out of 10, Exceptional, (4)
"We had a small group of adults and kids stay for the night. This house had plenty of space with the upstairs and downstairs living room and large bedrooms. The pool/air hockey table was fun for everyone and the large, fenced in yard gave the kids plenty of space to run around. Ari and Sri were amazing hosts! They quickly answered any messages, provided easy check-in and check-out instructions, and so kindly provided us with ice cream for the kids in the freezer! Overall we had a wonderful stay...
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
Sal's Place-Close to Tourism, Private Yard, Pool!
Pool

Sal's Place-Close to Tourism, Private Yard, Pool!

Sal's Place-Close to Tourism, Private Yard, Pool!
Charming Cape 🌞 With Beach Pass Included, Close to Beaches and Downtown
Fridge, microwave, oven, stovetop

Charming Cape 🌞 With Beach Pass Included, Close to Beaches and Downtown

9.4 out of 10, Exceptional, (10)
"Very beautiful and clean house and yard. The house is on a busy street but backyard is quite a nice oasis."
Charming Cape 🌞 With Beach Pass Included, Close to Beaches and Downtown
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (28)
"Great location and nice house! "
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!
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

Oak Bluffs - Quiet neighborhood

Oak Bluffs - Quiet neighborhood

10/10 Excellent
"Check-in was just as described and house was easy to find. Bill was easy to communicate with and allowed us to leave luggage early on the property (not in, to be clear!) so we could get to the beach. The house is quaint, completely functional and the location is great for biking and walking to OB, ten and twenty minutes respectively. The neighborhood is quiet and not far from Tony’s Market. Remember to rent your sheets and towels!"
Gizele R. 3-night trip
Posted 8 hours ago
Oak Bluffs - Quiet neighborhood