The Best Airbnb Deals in
Oak Bluffs, Massachusetts
Save money on your trip by finding the biggest discounts for top-rated Airbnb rentals in Oak Bluffs, Massachusetts. Enter your travel dates to find the best deals!
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AirDNA Score: 85
$275/night
AirDNA Score: 84
$649/night
The Oak Bluffs House - Walk to Beach & Town
2 beds
2.5 baths
6 guests
Average Price:
$1116
42% Cheaper
than normal
AirDNA Score: 79
$595/night
Victorian Oasis: Driveway, hot tub, grill & more
1 bed
1 bath
4 guests
Average Price:
$469
27% More
than normal
AirDNA Score: 74
$189/night
Stunning private apartment walk to everything!111C
1 bed
1 bath
4 guests
Average Price:
$375
50% Cheaper
than normal
AirDNA Score: 71
$199/night
Sunny Studio Apartment on Martha''s Vineyard
1 bed
1 bath
2 guests
Average Price:
$354
44% Cheaper
than normal
AirDNA Score: 71
$150/night
Studio apt in newly built barn
studio
1 bath
3 guests
Average Price:
$255
41% Cheaper
than normal
AirDNA Score: 69
$325/night
Beautiful 3 bedroom in Oak Bluffs, walk to beach
3 beds
2.5 baths
8 guests
Average Price:
$404
20% Cheaper
than normal
AirDNA Score: 67
$550/night
Downtown Oak Bluffs, First Floor Harbor House.
1 bed
1 bath
3 guests
Average Price:
$548
0% Cheaper
than normal
AirDNA Score: 66
$1300/night
Modern 5-bd, 4.5-bth home. Now booking for 2024!
5 beds
4.5 baths
12 guests
Average Price:
$1535
15% Cheaper
than normal
AirDNA Score: 66
$1140/night
Historic 1800''s House In Town/Beach
3 beds
2 baths
8 guests
Average Price:
$1443
21% Cheaper
than normal
AirDNA Score: 65
$315/night
AirDNA Score: 65
$749/night
Martha''s Vineyard Oak Bluffs Contemporary House
3 beds
2 baths
6 guests
Average Price:
$822
9% Cheaper
than normal
AirDNA Score: 65
$495/night
Vineyard Stroll
3 beds
2.5 baths
8 guests
Average Price:
$785
37% Cheaper
than normal
AirDNA Score: 64
$229/night
WATERFRONT PENTHOUSE OAK BLUFFS
studio
1 bath
2 guests
Average Price:
$431
47% Cheaper
than normal
AirDNA Score: 64
$219/night
Central location for your vacation
2 beds
1 bath
6 guests
Average Price:
$312
30% Cheaper
than normal
AirDNA Score: 64
$400/night
Downtown Oak Bluffs, 2nd floor Harbor house.
2 beds
1 bath
4 guests
Average Price:
$600
33% Cheaper
than normal
AirDNA Score: 61
$675/night
3 beds, 3 baths 1.5 Miles to Downtown and Beaches!
3 beds
3 baths
6 guests
Average Price:
$910
26% Cheaper
than normal
AirDNA Score: 61
$1000/night
Private Heated Pool, Wifi, AC, Grill & Firepit
5 beds
4.5 baths
16 guests
Average Price:
$3418
71% Cheaper
than normal
AirDNA Score: 61
$375/night
AirDNA Score: 61
$375/night
Sea View Waterfront Beachfront Apartment
1 bed
1 bath
3 guests
Average Price:
$417
10% Cheaper
than normal
AirDNA Score: 59
$211/night
Dog-friendly Studio Close to Beach | Tennis | Pool
studio
1 bath
4 guests
Average Price:
$234
10% Cheaper
than normal
AirDNA Score: 59
$2200/night
Chic Waterfront. 4Bd/4.5bth, Sleeps 11, kayaks A/C
4 beds
4.5 baths
11 guests
Average Price:
$2315
5% Cheaper
than normal
AirDNA Score: 59
$400/night
AirDNA Score: 58
$549/night
impeccable cottage STEPS to downtown OB & beach!
3 beds
1 bath
7 guests
Average Price:
$640
14% Cheaper
than normal
AirDNA Score: 58
$857/night
Newly Renovated Walk Town Oak Bluffs 4B/3b AC
4 beds
3 baths
9 guests
Average Price:
$1044
18% Cheaper
than normal
AirDNA Score: 58
$999/night
CENTRAL AIR!! WALK EVERYWHERE!
5 beds
3 baths
8 guests
Average Price:
$1077
7% Cheaper
than normal
AirDNA Score: 58
$328/night
Charming 1BR | Patio | Pool | Tennis
1 bed
1.5 baths
6 guests
Average Price:
$347
5% Cheaper
than normal
AirDNA Score: 57
$232/night
Dog-friendly Studio Near Beach | Pool | Tennis
studio
1 bath
4 guests
Average Price:
$239
3% Cheaper
than normal
AirDNA Score: 57
$429/night
2BR Island Inn Dog Friendly | Pool | Deck
2 beds
2 baths
6 guests
Average Price:
$446
4% Cheaper
than normal
AirDNA Score: 57
$295/night
Vineyard Cottage Charm, Walk to Beach, Mile toTown
2 beds
1 bath
6 guests
Average Price:
$442
33% Cheaper
than normal
AirDNA Score: 56
$495/night
Oak Bluffs Walk to Town
2 beds
2.5 baths
8 guests
Average Price:
$770
36% Cheaper
than normal
AirDNA Score: 55
$300/night
Mermaid Cottage with hot tub
1 bed
1 bath
4 guests
Average Price:
$288
4% More
than normal
AirDNA Score: 52
$462/night
Adorable 2BR Island Inn | Pool | Deck | Firepit
2 beds
2 baths
6 guests
Average Price:
$482
4% Cheaper
than normal
AirDNA Score: 52
$900/night
Oceanview Martha''s Vineyard
4 beds
4.5 baths
9 guests
Average Price:
$996
10% Cheaper
than normal
AirDNA Score: 52
$399/night
Martha’s Vineyard Cottage - Walk to Town and Beach
2 beds
1 bath
4 guests
Average Price:
$546
27% Cheaper
than normal
AirDNA Score: 52
$550/night
In Town Oak Bluffs Cottage - Walk to Everything!
5 beds
1.5 baths
10 guests
Average Price:
$1023
46% Cheaper
than normal
AirDNA Score: 51
$1900/night
The Island Collection MV: Seascape
7 beds
4 baths
14 guests
Average Price:
$2117
10% Cheaper
than normal
AirDNA Score: 51
$950/night
AirDNA Score: 51
$575/night
FABULOUS OCEAN VIEWS-Oak Bluffs Condo Across Beach
2 beds
2 baths
4 guests
Average Price:
$715
20% Cheaper
than normal
AirDNA Score: 51
$1850/night
NEW Modern Waterfront Beauty! "The Harper House"
4 beds
2.5 baths
8 guests
Average Price:
$2066
10% Cheaper
than normal
AirDNA Score: 50
$1575/night
Martha''s Vineyard Dream Beach House
5 beds
4 baths
10 guests
Average Price:
$1380
14% More
than normal
AirDNA Score: 50
$600/night
LOCATION LOCATION!! Ocean- View TOP Floor Condo
2 beds
2 baths
4 guests
Average Price:
$691
13% Cheaper
than normal
AirDNA Score: 50
$699/night
Play, Pace, Peace (and Parking too!)!
5 beds
2 baths
8 guests
Average Price:
$937
25% Cheaper
than normal
AirDNA Score: 48
$500/night
A quaint Martha''s Vineyard Island Retreat
3 beds
2 baths
6 guests
Average Price:
$543
8% Cheaper
than normal
AirDNA Score: 47
$900/night
The quintessential MV home. Now booking for 2024!
4 beds
4 baths
9 guests
Average Price:
$1240
27% Cheaper
than normal
AirDNA Score: 46
$10000/night
The Park Estate: Your Martha''s Vineyard Getaway!
6 beds
5 baths
16 guests
Average Price:
$8650
16% More
than normal
AirDNA Score: 46
$875/night
Newly renovated, New Pool 2022! Rest, Relax, Renew
4 beds
2.5 baths
9 guests
Average Price:
$1470
40% Cheaper
than normal
AirDNA Score: 46
$294/night
2BR Lakefront | Deck | Washer/Dryer
2 beds
1 bath
4 guests
Average Price:
$347
15% Cheaper
than normal
AirDNA Score: 45
$500/night
Martha''s Vineyard Oak Bluffs June July Only
4 beds
2 baths
7 guests
Average Price:
$545
8% Cheaper
than normal
AirDNA Score: 44
$350/night
Martha’s Vineyard at its Best!
3 beds
2.5 baths
6 guests
Average Price:
$455
23% Cheaper
than normal
AirDNA Score: 43
$156/night
Absolute Best Location on the Island
2 beds
1 bath
5 guests
Average Price:
$304
49% Cheaper
than normal
AirDNA Score: 41
$500/night
Martha''s Vineyard house near Lagoon Pond Beach
2 beds
2 baths
4 guests
Average Price:
$517
3% Cheaper
than normal
AirDNA Score: 39
$880/night
AirDNA Score: 39
$800/night
East Chop Charmer- views, private beach, sunsets!
3 beds
2 baths
9 guests
Average Price:
$972
18% Cheaper
than normal
AirDNA Score: 39
$299/night
Cozy Vacation Getaway On Bike Path
3 beds
1 bath
6 guests
Average Price:
$454
34% Cheaper
than normal
AirDNA Score: 38
$143/night
One Bed Apartment 0.8 miles to Farm Neck Golf!!
1 bed
1 bath
4 guests
Average Price:
$371
61% Cheaper
than normal
AirDNA Score: 38
$255/night
Cozy 1BR Island Inn | Patio | Pool
1 bed
1 bath
2 guests
Average Price:
$261
2% Cheaper
than normal
AirDNA Score: 37
$300/night
AirDNA Score: 37
$585/night
Spectacular Martha''s Vineyard Island Home!
3 beds
2.5 baths
10 guests
Average Price:
$708
17% Cheaper
than normal
AirDNA Score: 37
$379/night
Renovated 2BR Island Inn | Pool | Deck
2 beds
2 baths
6 guests
Average Price:
$438
13% Cheaper
than normal
AirDNA Score: 37
$396/night
Charming 2BR Waterview Island Inn | Pool | Deck
2 beds
2 baths
5 guests
Average Price:
$429
8% Cheaper
than normal
AirDNA Score: 37
$800/night
Lovely 4 BR house steps from beach
4 beds
2 baths
7 guests
Average Price:
$946
15% Cheaper
than normal
AirDNA Score: 32
$373/night
Stylish 2BR Island Inn | Pool | Deck | Firepit
2 beds
1.5 baths
6 guests
Average Price:
$390
4% Cheaper
than normal
AirDNA Score: 32
$239/night
Cute 2BR Island Inn | Patio | Pool
2 beds
1 bath
6 guests
Average Price:
$276
13% Cheaper
than normal
AirDNA Score: 31
$388/night
Cozy 2BR Island Inn Dog Friendly | Pool | Deck
2 beds
1.5 baths
6 guests
Average Price:
$403
4% Cheaper
than normal
AirDNA Score: 30
$402/night
Superb 2BR Island Inn | Pool | Deck | Firepit
2 beds
1.5 baths
6 guests
Average Price:
$414
3% Cheaper
than normal
AirDNA Score: 30
$258/night
Romantic Studio Island Inn | Balcony | Pool
studio
1 bath
4 guests
Average Price:
$266
3% Cheaper
than normal
AirDNA Score: 30
$258/night
Welcoming Studio Island Inn | Patio | Pool
studio
1 bath
4 guests
Average Price:
$264
2% Cheaper
than normal
AirDNA Score: 30
$372/night
1BR Island Inn 1st-Floor | Balcony | Pool
1 bed
1.5 baths
6 guests
Average Price:
$381
2% Cheaper
than normal
AirDNA Score: 30
$277/night
Dog-friendly 1st-Floor Seaside 1BR Cottage | Pool
1 bed
1 bath
4 guests
Average Price:
$290
4% Cheaper
than normal
AirDNA Score: 29
$372/night
Coastal 1BR Island Inn | Patio | Pool
1 bed
1.5 baths
6 guests
Average Price:
$381
2% Cheaper
than normal
AirDNA Score: 29
$324/night
Lovely 1BR Close to Beach/Golf | Pool | Tennis
1 bed
1.5 baths
4 guests
Average Price:
$334
3% Cheaper
than normal
AirDNA Score: 29
$350/night
Charming 2+ BR Cottage on Brush Pond
3 beds
1 bath
6 guests
Average Price:
$434
19% Cheaper
than normal
AirDNA Score: 29
$419/night
Comfortable 2BR Island Inn | Pool | Deck
2 beds
2 baths
6 guests
Average Price:
$449
7% Cheaper
than normal
AirDNA Score: 29
$255/night
Perfect 2BR Island Inn | Patio | Pool
2 beds
1 bath
4 guests
Average Price:
$291
12% Cheaper
than normal
AirDNA Score: 29
$244/night
Charming Studio by Beach | Pool | Tennis
studio
1 bath
4 guests
Average Price:
$253
4% Cheaper
than normal
AirDNA Score: 25
$381/night
Charming 3BR | Deck | W/D | Near Pond/Boat Launch
3 beds
1.5 baths
7 guests
Average Price:
$462
18% Cheaper
than normal
AirDNA Score: 25
$441/night
Lovely 2BR Island Inn | Pool | Deck | Firepit
2 beds
2 baths
6 guests
Average Price:
$455
3% Cheaper
than normal
AirDNA Score: 25
$372/night
Lovely 1BR Half Mile to Beach | Pool | Tennis
1 bed
1.5 baths
6 guests
Average Price:
$384
3% Cheaper
than normal
AirDNA Score: 24
$303/night
3BR Martha''s Vineyard | Patio | W/D
3 beds
1 bath
6 guests
Average Price:
$442
31% Cheaper
than normal
AirDNA Score: 24
$368/night
Charming 1BR Island Inn | Deck | Pool
1 bed
1.5 baths
6 guests
Average Price:
$381
3% Cheaper
than normal
AirDNA Score: 23
$641/night
Luxury 5BR | Pool | Fireplace | Balcony
5 beds
4.5 baths
10 guests
Average Price:
$920
30% Cheaper
than normal
AirDNA Score: 23
$373/night
Dog-friendly 1st-Floor 1BR | Pool | Tennis
1 bed
1.5 baths
5 guests
Average Price:
$377
1% Cheaper
than normal
AirDNA Score: 22
$714/night
Great Rental on Martha''s Vineyard - Weekly
4 beds
2 baths
8 guests
Average Price:
$731
2% Cheaper
than normal
AirDNA Score: 22
$257/night
Convenient Studio Island Inn | Deck | Pool
studio
1 bath
4 guests
Average Price:
$261
2% Cheaper
than normal
AirDNA Score: 22
$395/night
Sweet Suite Close to Beach and Town
1 bed
1 bath
2 guests
Average Price:
$409
3% Cheaper
than normal
AirDNA Score: 22
$344/night
Serene 4BR Dog Friendly | Patio | W/D
4 beds
2 baths
8 guests
Average Price:
$446
23% Cheaper
than normal
AirDNA Score: 22
$383/night
Spacious 2BR Island Inn | Pool | Deck | Firepit
2 beds
1.5 baths
6 guests
Average Price:
$406
6% Cheaper
than normal
AirDNA Score: 22
$405/night
Sunny 2BR Island Inn | Pool | Deck | Firepit
2 beds
2 baths
4 guests
Average Price:
$425
5% Cheaper
than normal
AirDNA Score: 22
$324/night
Sunny 1BR Island Inn | Patio | Pool
1 bed
1.5 baths
6 guests
Average Price:
$350
7% Cheaper
than normal
AirDNA Score: 22
$257/night
Contemporary Studio Island Inn | Patio | Pool
studio
1 bath
4 guests
Average Price:
$263
2% Cheaper
than normal
AirDNA Score: 22
$324/night
1BR Island Inn | Deck | Pool | Firepit
1 bed
1.5 baths
4 guests
Average Price:
$338
4% Cheaper
than normal
AirDNA Score: 22
$363/night
Convenient 1BR Island Inn | Deck | Pool
1 bed
1.5 baths
6 guests
Average Price:
$381
5% Cheaper
than normal
AirDNA Score: 21
$549/night
Spacious 4BR | Dog-friendly | Fenced yard
4 beds
0 bath
10 guests
Average Price:
$602
9% Cheaper
than normal
AirDNA Score: 21
$379/night
2BR Waterview Island Inn Dog Friendly | Pool
2 beds
1.5 baths
6 guests
Average Price:
$390
3% Cheaper
than normal
AirDNA Score: 21
$251/night
Cozy Studio Close to Beach/Town | Pool | Tennis
studio
1 bath
4 guests
Average Price:
$260
3% Cheaper
than normal
AirDNA Score: 16
$450/night
Martha’s Vineyard Peaceful Get Away
2 beds
1.5 baths
4 guests
Average Price:
$503
11% Cheaper
than normal
AirDNA Score: 15
$100/night
Separate entrance 3 beds, bath and kitchenette
1 bed
1 bath
3 guests
Average Price:
$378
74% Cheaper
than normal
AirDNA Score: 15
$848/night
Aunt Clara''s Cottage ~ Your Beautiful Island Home!
4 beds
3 baths
8 guests
Average Price:
$906
6% Cheaper
than normal
AirDNA Score: 15
$1000/night
Privacy and serenity. An ideal vacation spot
3 beds
2 baths
7 guests
Average Price:
$863
16% More
than normal