Holiday Homes in Oak Bluffs

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Holiday Homes in Oak Bluffs

Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown
Beach nearby, sun-loungers, beach towels

Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

10.0 out of 10, Exceptional, (154)
"This place has everything you need for a very pleasant stay in Falmouth. Communication was great. Check-in was flawless once I figured out which key was which. The location is in a nice quiet neighborhood and just minutes from everything anyone could need, including a GREAT patisserie/boulangerie that I wish we would have found two days earlier. The house itself is a bit older with a few minor, older house issues, none of which are bothersome at all. It is very well equipped. None of the...
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown
Private suite upstairs: bedroom, office, TV room, bathroom & a large deck.
Terrace/patio

Private suite upstairs: bedroom, office, TV room, bathroom & a large deck.

10.0 out of 10, Exceptional, (24)
"Nice upper suite. Clean rooms. It was nice that linens were provided. It had a small mini fridge and small microwave stacked on a table. A table to sit at would have been nice. 2 small mugs and 2 plastic wine glasses were supplied as well. I stayed for 6 nights so I just kept rinsing out my mug. 2 separate AC units provided comfortable temperature. Nice quiet area. The deck was nice. It was wet from condensation in the morning and then hot in afternoon with full sun so I didn’t use it. ...
Private suite upstairs: bedroom, office, TV room, bathroom & a large deck.
Spacious cape house near Craigville Beach, downtown Centerville, Hyannis & more!
Outdoor dining

Spacious cape house near Craigville Beach, downtown Centerville, Hyannis & more!

9.6 out of 10, Exceptional, (15)
"A group of friends and I had a lovely long weekend stay here. The yard is so big and perfect for games and relaxing, and the house is close to several beaches, mini golf, restaurants, ice cream, etc. The layout is kind of weird, but we had plenty of space for everything. Would stay here again!"
Spacious cape house near Craigville Beach, downtown Centerville, Hyannis & more!
Immaculate Cape Cod Family Retreat- minutes from Ponds, Lakes, and Ocean!
Fridge, microwave, oven, stovetop

Immaculate Cape Cod Family Retreat- minutes from Ponds, Lakes, and Ocean!

10.0 out of 10, Exceptional, (41)
"The house was beautifully clean and well equipped . The central location meant we could fully explore all areas , and enjoy the local hospitality. I would highly recommend this property and its host to friends and family .its a 10 out of 10 from us."
Immaculate Cape Cod Family Retreat- minutes from Ponds, Lakes, and Ocean!
Stunning Lake Front House with Private Beach
Fridge, microwave, oven, stovetop

Stunning Lake Front House with Private Beach

8.8 out of 10, Excellent, (5)
"We stayed for a weekend with a few adults and a bunch of teenagers - great layout for socializing with the bedrooms on three floors. Lake is gorgeous. Very clean."
The price is AU$1,742
includes taxes & fees
2 Dec - 3 Dec
Stunning Lake Front House with Private Beach
STEP DIRECTLY ONTO YOUR PRIVATE MAUSHOP VILLAGE BEACH AT THIS SEASIDE TOWNHOME
Exterior

STEP DIRECTLY ONTO YOUR PRIVATE MAUSHOP VILLAGE BEACH AT THIS SEASIDE TOWNHOME

2.0 star property
10.0 out of 10, Exceptional, (3)
"This beach town home is elegant and charming. The location is unbeatable; we enjoyed easy access to the beach, as well as nearby shops and restaurants. We spent our days beaching it up, and exploring the local area (all fun stuff within walking distance). From the moment we booked to the day we departed, the host always had prompt, friendly and helpful communication, and provided us with great recommendations for things to do for the whole family. THANK YOU FOR AN UNFORGETTABLE vacation, we just...
STEP DIRECTLY ONTO YOUR PRIVATE MAUSHOP VILLAGE BEACH AT THIS SEASIDE TOWNHOME
Dream coastal dog-friendly vacation 4-bedroom home. Steps from Keyes Beach!
Beach nearby, sun-loungers, beach towels

Dream coastal dog-friendly vacation 4-bedroom home. Steps from Keyes Beach!

9.8 out of 10, Exceptional, (144)
"The house was very nice and the perfect layout for our gang. The check out pricess briught some grumbles from some family membersas well as the 10 AM check out. I explained its a lot of house to clean before a new group at 4PM. A relative that lives on the Cape said the other side of Sea Street is a bit shady, which is why I gave the 4 star for location. "
Dream coastal dog-friendly vacation 4-bedroom home. Steps from Keyes Beach!
Cozy Cape home with outdoor shower and deck - minutes to beach
Terrace/patio

Cozy Cape home with outdoor shower and deck - minutes to beach

9.8 out of 10, Exceptional, (60)
"House was perfect. Wonderful location. Enjoyed stay so much."
Cozy Cape home with outdoor shower and deck - minutes to beach
Ocean Views From Every Room, Beach 30 Seconds Away!
Exterior

Ocean Views From Every Room, Beach 30 Seconds Away!

10.0 out of 10, Exceptional, (100)
"This was an unusual situation in that we were getting together to honor and remember three immediate family members we'd lost over the past four years. Cape Cod has always been a special place to us, Hyannis in particular. So there was a lot of pressure as the location could make or break the experience. In making the arrangements I assumed the description of the property had to be slightly exaggerated but the pictures were beautiful, it was pet friendly, and the reviews were all very positive....
Ocean Views From Every Room, Beach 30 Seconds Away!
Immaculate Home, 2 Acres, Short Walk To Beach!
Fridge, microwave, oven, stovetop

Immaculate Home, 2 Acres, Short Walk To Beach!

10.0 out of 10, Exceptional, (6)
"Our family really enjoyed our stay. Check in and out was easy. House was spacious with lots of room for everyone. Area was gorgeous with plenty to do. Many thanks!"
Immaculate Home, 2 Acres, Short Walk To Beach!
Popponesset Exclusive- Heated Pool, Fire Pit & Hot Tub and Cabana
Smart TV, fireplace, books

Popponesset Exclusive- Heated Pool, Fire Pit & Hot Tub and Cabana

10.0 out of 10, Exceptional, (68)
"We attended a wedding Friday night. The location of the house was within 1 mile. Great location. The property was beautiful and we couldn’t be happier with our stay. "
Popponesset Exclusive- Heated Pool, Fire Pit & Hot Tub and Cabana
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (188)
"The house was as advertised! Spacious, clean, comfy beds and close to town and beach. Very nice stay. We would definitely rent again! Thank you!"
The price is AU$897
includes taxes & fees
4 Dec - 5 Dec
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
Fridge, microwave, oven, stovetop

Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry

9.6 out of 10, Exceptional, (46)
"Lovely visit "
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
Cozy 2 bdrm sleeps 5. Walk to Electric Av Beach, Main St, Canal, Mass Maritime.
Exterior

Cozy 2 bdrm sleeps 5. Walk to Electric Av Beach, Main St, Canal, Mass Maritime.

10.0 out of 10, Exceptional, (11)
"This property has everything you need and more. It is very well organized, and directions are there for every question you might have. Would definably stay again. Our son goes to MMA and it's within walking distance, on a nice day. "
Cozy 2 bdrm sleeps 5. Walk to Electric Av Beach, Main St, Canal, Mass Maritime.
Your Oasis Awaits
Property grounds

Your Oasis Awaits

9.8 out of 10, Exceptional, (38)
"This is a lovely property near Mashpee. It is very close to the beach and part of a larger resort community. Very convenient to other areas (most of the Cape is within an hour's drive--Ptown slightly longer). Extremely quiet and comfortable. Lovely outdoor seating area. Very cozy. "
Your Oasis Awaits
First Time Available to Rent in 40 Years
Beach nearby, sun-loungers, beach towels

First Time Available to Rent in 40 Years

9.2 out of 10, Wonderful, (35)
"This house was absolutely perfect for a week-stay on the Cape. The neighborhood was quiet, and the beach was just a few houses away, visible from couch in the living room. The house was clean and comfortable with most everything needed for our stay The property loses one star because there is some unfinished work in the house. One of the bedframes was really loose, but the host was able to come by and tighten it up. The bathroom is missing the towel rack and the wall where it was removed hasn't...
First Time Available to Rent in 40 Years
Central Woods Hole Village Waterfront: Autumn Now Discounted 20%
Beach nearby, sun-loungers, beach towels

Central Woods Hole Village Waterfront: Autumn Now Discounted 20%

10.0 out of 10, Exceptional, (105)
"Deserves a10! Beautiful home,beautiful views! Everything you need is right there. Highly recommend ❤️"
Central Woods Hole Village Waterfront: Autumn Now Discounted 20%
In Ground Pool, A/C, 4+BR, 3BA, Wifi, Game Room. Sleeps 10-12, strong wifi
Outdoor pool

In Ground Pool, A/C, 4+BR, 3BA, Wifi, Game Room. Sleeps 10-12, strong wifi

9.0 out of 10, Wonderful, (53)
"This home and yard are bigger than I thought they would be looking at the pictures, making this property perfect for hosting a large group. Ample space in the bedrooms, multiple bathrooms, and kitchen is fully equipped. Also the huge mudroom was a surprise favorite feature of ours - great for keeping everything organized and out of the main living areas. The pool was amazing and the yard behind is large, perfect for hosting outdoor activities. The location centers you between tons of fun local...
In Ground Pool, A/C, 4+BR, 3BA, Wifi, Game Room. Sleeps 10-12, strong wifi
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Property grounds

Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!

9.8 out of 10, Exceptional, (37)
"We enjoyed our time here. The house sits is in a very quiet landscape. Remote and relaxing. Just what we have been looking for. Quick drive to beautiful beaches and the cliffs near Gays Lighthouse. Highly recommend this gem."
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Island bliss located near shops and eateries-several island beaches also nearby
Marina

Island bliss located near shops and eateries-several island beaches also nearby

9.0 out of 10, Wonderful, (29)
"Oak Bluffs is a beautiful place. The home was perfect for us with two bathrooms and a kitchen open to the living room. We only used two out of three bedrooms. We walked to town which was about one and a half miles."
Island bliss located near shops and eateries-several island beaches also nearby
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.
Don't see what you're looking for?
See all available properties in Oak Bluffs
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Oak Bluffs

Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
Fridge, microwave, oven, stovetop

Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

8.4 out of 10, Very good, (33)
"Perfect escape for three actors coming from a project with an unexpected few days off. We booked last minute and were thrilled to be able to have some things so centrally located"
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
Romantic seaside getaway with pool & tennis courts - dog-friendly
Iron/ironing board, free Internet, bed sheets

Romantic seaside getaway with pool & tennis courts - dog-friendly

9.6 out of 10, Exceptional, (42)
"Nice inn with comfortable and clean units. Not spectacular, but it's one of the few affordable places on the island. Some people might be put off by the location, a mile south of Oaks Bluff. But it's got Noman's, a great restaurant with live music, and it's right on the bus line. Also you can walk 15 minutes to the beach. Units not soundproof, you can here some noise from your neighbors. Great pool and tennis courts."
Romantic seaside getaway with pool & tennis courts - dog-friendly
Luxury home with private pool & foosball - near 3 towns & many beaches
Pool

Luxury home with private pool & foosball - near 3 towns & many beaches

8.6 out of 10, Excellent, (36)
"I recently stayed in this lovely OB home with my family. It was me and 9 other people, and there was plenty of room for everyone. The photos are accurate. The pool was clean and heated. The house is located in a private, wooded area but conveniently located to OB, Edgartown, the airport and beaches. The interior/furniture were so cozy. The house came equipped with enough plates, dishes, pots, pans, utensil, towels, etc. It would be helpful if the house came with a book of instructions, so we'd...
Luxury home with private pool & foosball - near 3 towns & many beaches
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals