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: 86
$183/night
Walk to Town, beach and amazing location 113A
2 beds
1.5 baths
4 guests
Average Price:
$588
69% Cheaper
than normal
AirDNA Score: 86
$140/night
Lovely 2 BR Oak Bluffs Apartment
2 beds
1 bath
4 guests
Average Price:
$183
23% Cheaper
than normal
AirDNA Score: 85
$175/night
AirDNA Score: 84
$553/night
The Oak Bluffs House - Walk to Beach & Town
2 beds
2.5 baths
6 guests
Average Price:
$960
42% Cheaper
than normal
AirDNA Score: 79
$316/night
Sweet little post and beam
2 beds
1.5 baths
2 guests
Average Price:
$368
14% Cheaper
than normal
AirDNA Score: 79
$183/night
Best location!!! Beach & Town 5min walk 113R
1 bed
1 bath
4 guests
Average Price:
$344
47% Cheaper
than normal
AirDNA Score: 79
$183/night
Stunning. Walk to Beach, Town and Harbor 113B
1 bed
1 bath
2 guests
Average Price:
$388
53% Cheaper
than normal
AirDNA Score: 79
$183/night
Beautiful clean walk to beach and all of downtown!
1 bed
1 bath
4 guests
Average Price:
$396
54% Cheaper
than normal
AirDNA Score: 79
$795/night
Victorian Oasis: Driveway, hot tub, grill & more
1 bed
1 bath
4 guests
Average Price:
$691
15% More
than normal
AirDNA Score: 74
$159/night
Beautiful private apartment walk to everything!
1 bed
1 bath
4 guests
Average Price:
$489
67% Cheaper
than normal
AirDNA Score: 71
$175/night
In-Town Retreat: Deck, Walk to beach, a Gem!
1 bed
1.5 baths
4 guests
Average Price:
$329
47% Cheaper
than normal
AirDNA Score: 71
$183/night
Beautiful walk to beach and Downtown Oak Bluffs!
1 bed
1 bath
4 guests
Average Price:
$440
58% Cheaper
than normal
AirDNA Score: 71
$150/night
Studio apt in newly built barn
studio
1 bath
3 guests
Average Price:
$237
37% Cheaper
than normal
AirDNA Score: 71
$183/night
Beautiful stroll to beach and all of downtown!
1 bed
1 bath
4 guests
Average Price:
$292
37% Cheaper
than normal
AirDNA Score: 69
$300/night
Beautiful 3 bedroom in Oak Bluffs, walk to beach
3 beds
2.5 baths
8 guests
Average Price:
$426
30% Cheaper
than normal
AirDNA Score: 66
$1117/night
Modern 5-bd, 4.5-bth home. Now booking for 2024!
5 beds
4.5 baths
12 guests
Average Price:
$1313
15% Cheaper
than normal
AirDNA Score: 66
$1495/night
Historic 1800''s House In Town/Beach
3 beds
2 baths
8 guests
Average Price:
$1402
7% More
than normal
AirDNA Score: 65
$350/night
Historic East Chop Beach House
4 beds
2 baths
7 guests
Average Price:
$549
36% Cheaper
than normal
AirDNA Score: 65
$197/night
East Chop Cottage - walk to lighthouse & beach!
1 bed
0 bath
2 guests
Average Price:
$437
55% Cheaper
than normal
AirDNA Score: 65
$479/night
Private Waterfront, Beach, 90' Dock, Renovated
3 beds
1 bath
6 guests
Average Price:
$536
11% Cheaper
than normal
AirDNA Score: 65
$447/night
Vineyard Getaway! Spacious Home Walk to Oak Bluffs
3 beds
2.5 baths
10 guests
Average Price:
$803
44% Cheaper
than normal
AirDNA Score: 65
$695/night
Martha's Vineyard Oak Bluffs Contemporary House
3 beds
2 baths
6 guests
Average Price:
$847
18% Cheaper
than normal
AirDNA Score: 64
$225/night
WATERFRONT PENTHOUSE OAK BLUFFS
studio
1 bath
2 guests
Average Price:
$407
45% Cheaper
than normal
AirDNA Score: 61
$250/night
AirDNA Score: 61
$350/night
Sea View Waterfront Beachfront Apartment
1 bed
1 bath
3 guests
Average Price:
$425
18% Cheaper
than normal
AirDNA Score: 59
$224/night
Dog-friendly Studio Close to Beach | Tennis | Pool
studio
1 bath
4 guests
Average Price:
$252
11% Cheaper
than normal
AirDNA Score: 59
$210/night
Prime Studio Island Inn | Patio | Pool
studio
1 bath
4 guests
Average Price:
$290
28% Cheaper
than normal
AirDNA Score: 59
$255/night
Dog-friendly 1st-Floor 1BR Near Beach/Park | Pool
1 bed
1 bath
4 guests
Average Price:
$387
34% Cheaper
than normal
AirDNA Score: 59
$900/night
Chic Waterfront 4Bd/4.5bth, Sleeps 11, kayaks A/C
4 beds
4.5 baths
11 guests
Average Price:
$1778
49% Cheaper
than normal
AirDNA Score: 59
$828/night
An Oak Bluffs cottage in town
4 beds
2 baths
8 guests
Average Price:
$880
6% Cheaper
than normal
AirDNA Score: 58
$399/night
impeccable cottage STEPS to downtown OB & beach!
3 beds
1 bath
7 guests
Average Price:
$601
34% Cheaper
than normal
AirDNA Score: 58
$730/night
CENTRAL AIR!! WALK EVERYWHERE!
5 beds
3 baths
8 guests
Average Price:
$861
15% Cheaper
than normal
AirDNA Score: 58
$712/night
Newly Renovated Walk Town Oak Bluffs 4B/3b AC
4 beds
3 baths
9 guests
Average Price:
$1131
37% Cheaper
than normal
AirDNA Score: 58
$428/night
Beautiful Home in Great Location
3 beds
2 baths
6 guests
Average Price:
$637
33% Cheaper
than normal
AirDNA Score: 58
$209/night
Charming Studio Island Inn | Deck | Pool
studio
1 bath
4 guests
Average Price:
$279
25% Cheaper
than normal
AirDNA Score: 58
$204/night
Comfy Studio Island Inn | Patio | Pool
studio
1 bath
4 guests
Average Price:
$291
30% Cheaper
than normal
AirDNA Score: 58
$293/night
Charming 1BR | Patio | Pool | Tennis
1 bed
1.5 baths
6 guests
Average Price:
$407
28% Cheaper
than normal
AirDNA Score: 57
$220/night
Dog-friendly Studio Near Beach | Pool | Tennis
studio
1 bath
4 guests
Average Price:
$287
23% Cheaper
than normal
AirDNA Score: 57
$359/night
2BR Island Inn Dog Friendly | Pool | Deck
2 beds
2 baths
6 guests
Average Price:
$553
35% Cheaper
than normal
AirDNA Score: 57
$259/night
Martha's Vineyard studio apartment
1 bed
1 bath
2 guests
Average Price:
$296
12% Cheaper
than normal
AirDNA Score: 55
$250/night
AirDNA Score: 54
$400/night
Oak Bluffs near beaches & town, A/C,Jacuzzi,kayaks
4 beds
2.5 baths
10 guests
Average Price:
$454
12% Cheaper
than normal
AirDNA Score: 52
$422/night
Adorable 2BR Island Inn | Pool | Deck | Firepit
2 beds
2 baths
6 guests
Average Price:
$470
10% Cheaper
than normal
AirDNA Score: 52
$979/night
Oceanview Martha''s Vineyard
4 beds
4.5 baths
9 guests
Average Price:
$1010
3% Cheaper
than normal
AirDNA Score: 52
$2754/night
East Chop Waterview Farmhouse/Serene Getaway
6 beds
4.5 baths
10 guests
Average Price:
$3056
10% Cheaper
than normal
AirDNA Score: 51
$1306/night
The Island Collection MV: Seascape
7 beds
4 baths
14 guests
Average Price:
$2058
37% Cheaper
than normal
AirDNA Score: 51
$450/night
Serenity on Martha's Vineyard
2 beds
2 baths
5 guests
Average Price:
$503
11% Cheaper
than normal
AirDNA Score: 51
$700/night
Beautiful Martha's Vineyard Home
3 beds
2.5 baths
6 guests
Average Price:
$763
8% Cheaper
than normal
AirDNA Score: 51
$503/night
FABULOUS OCEAN VIEWS-Oak Bluffs Condo Across Beach
2 beds
2 baths
4 guests
Average Price:
$653
23% Cheaper
than normal
AirDNA Score: 51
$989/night
NEW Modern Waterfront Beauty! "The Harper House"
4 beds
2.5 baths
12 guests
Average Price:
$1651
40% Cheaper
than normal
AirDNA Score: 50
$985/night
Family Property with Pool, Hot Tub, and Pond
6 beds
4.5 baths
16 guests
Average Price:
$2221
56% Cheaper
than normal
AirDNA Score: 50
$650/night
LOCATION LOCATION!! Ocean- View TOP Floor Condo
2 beds
2 baths
4 guests
Average Price:
$686
5% Cheaper
than normal
AirDNA Score: 50
$599/night
Play, Pace, Peace (and Parking too!)!
5 beds
2 baths
8 guests
Average Price:
$885
32% Cheaper
than normal
AirDNA Score: 49
$951/night
Victorian charm, steps to beach
4 beds
3 baths
9 guests
Average Price:
$1320
28% Cheaper
than normal
AirDNA Score: 47
$1200/night
Martha's Vineyard Vacation Rental
5 beds
4.5 baths
10 guests
Average Price:
$1284
7% Cheaper
than normal
AirDNA Score: 47
$1000/night
Oak Bluffs Victorian Walk to Town & Beaches
5 beds
5.5 baths
12 guests
Average Price:
$1323
24% Cheaper
than normal
AirDNA Score: 46
$5000/night
The Park Estate: Your Martha's Vineyard Getaway!
6 beds
5 baths
16 guests
Average Price:
$6864
27% Cheaper
than normal
AirDNA Score: 46
$700/night
Luxury! Heated Pool & Spa!Tennis! Firepit! Hammock
4 beds
2.5 baths
9 guests
Average Price:
$1780
61% Cheaper
than normal
AirDNA Score: 46
$382/night
Classic Oak Bluffs Home In-Town: Price reduced!
4 beds
1.5 baths
8 guests
Average Price:
$577
34% Cheaper
than normal
AirDNA Score: 45
$395/night
Saltbox Cottage in Oak Bluffs
2 beds
1.5 baths
6 guests
Average Price:
$532
26% Cheaper
than normal
AirDNA Score: 45
$125/night
Sunny Private studio amazing deck kayaks & kitchen
1 bed
1 bath
2 guests
Average Price:
$287
56% Cheaper
than normal
AirDNA Score: 45
$450/night
Martha's Vineyard Oak Bluffs June July Only
4 beds
2 baths
7 guests
Average Price:
$547
18% Cheaper
than normal
AirDNA Score: 44
$300/night
September is Beautiful on the Vineyard!
3 beds
2.5 baths
6 guests
Average Price:
$558
46% Cheaper
than normal
AirDNA Score: 43
$210/night
Absolute Best Location on the Island
2 beds
1 bath
5 guests
Average Price:
$260
19% Cheaper
than normal
AirDNA Score: 43
$619/night
Vineyard Social
5 beds
4.5 baths
14 guests
Average Price:
$844
27% Cheaper
than normal
AirDNA Score: 41
$291/night
Martha's Vineyard house near Lagoon Pond Beach
2 beds
2 baths
4 guests
Average Price:
$470
38% Cheaper
than normal
AirDNA Score: 40
$452/night
Cozy, Clean, Bikes, Kayaks, Lagoon
3 beds
1 bath
7 guests
Average Price:
$479
6% Cheaper
than normal
AirDNA Score: 39
$891/night
AirDNA Score: 39
$600/night
Martha's Vineyard Waterfront- large home & yard
3 beds
2 baths
9 guests
Average Price:
$899
33% Cheaper
than normal
AirDNA Score: 39
$199/night
Cozy Vacation Getaway On Bike Path
3 beds
1 bath
6 guests
Average Price:
$413
52% Cheaper
than normal
AirDNA Score: 38
$162/night
Fantastic beach Ap 0.8 miles from Farm Neck Golf!
1 bed
1 bath
4 guests
Average Price:
$306
47% Cheaper
than normal
AirDNA Score: 38
$204/night
Cozy Dog Friendly Studio | Pool | Firepit | Tennis
studio
1 bath
4 guests
Average Price:
$292
30% Cheaper
than normal
AirDNA Score: 38
$400/night
The Beach Hive
3 beds
2.5 baths
8 guests
Average Price:
$461
13% Cheaper
than normal
AirDNA Score: 38
$255/night
Cozy 1BR Island Inn | Patio | Pool
1 bed
1 bath
2 guests
Average Price:
$369
31% Cheaper
than normal
AirDNA Score: 37
$385/night
Charming 2BR Waterview Island Inn | Pool | Deck
2 beds
2 baths
5 guests
Average Price:
$443
13% Cheaper
than normal
AirDNA Score: 37
$360/night
Renovated 2BR Island Inn | Pool | Deck
2 beds
2 baths
6 guests
Average Price:
$465
23% Cheaper
than normal
AirDNA Score: 37
$750/night
Lovely 4 BR house steps from beach
4 beds
2 baths
7 guests
Average Price:
$889
16% Cheaper
than normal
AirDNA Score: 35
$274/night
Downtown 4BR | Patio | Washer/Dryer
4 beds
3 baths
10 guests
Average Price:
$688
60% Cheaper
than normal
AirDNA Score: 32
$204/night
Romantic Studio Island Inn | Deck | Pool
studio
1 bath
4 guests
Average Price:
$294
31% Cheaper
than normal
AirDNA Score: 32
$366/night
Stylish 2BR Island Inn | Pool | Deck | Firepit
2 beds
1.5 baths
6 guests
Average Price:
$447
18% Cheaper
than normal
AirDNA Score: 32
$262/night
Cute 2BR Island Inn | Patio | Pool
2 beds
1 bath
4 guests
Average Price:
$271
3% Cheaper
than normal
AirDNA Score: 31
$204/night
Charming Studio Close to Beach | Pool | Tennis
studio
1 bath
2 guests
Average Price:
$255
20% Cheaper
than normal
AirDNA Score: 31
$207/night
Dog-friendly Studio Close to Beach | Pool | Tennis
studio
1 bath
4 guests
Average Price:
$296
30% Cheaper
than normal
AirDNA Score: 31
$335/night
Cozy 2BR Island Inn Dog Friendly | Pool | Deck
2 beds
1.5 baths
6 guests
Average Price:
$442
24% Cheaper
than normal
AirDNA Score: 31
$638/night
Oak Bluffs Cottage Near Town
4 beds
2 baths
8 guests
Average Price:
$1125
43% Cheaper
than normal
AirDNA Score: 30
$340/night
Superb 2BR Island Inn | Pool | Deck | Firepit
2 beds
1.5 baths
6 guests
Average Price:
$456
25% Cheaper
than normal
AirDNA Score: 30
$209/night
Romantic Studio Island Inn | Balcony | Pool
studio
1 bath
4 guests
Average Price:
$258
19% Cheaper
than normal
AirDNA Score: 30
$218/night
Welcoming Studio Island Inn | Patio | Pool
studio
1 bath
4 guests
Average Price:
$283
23% Cheaper
than normal
AirDNA Score: 30
$294/night
1BR Island Inn 1st-Floor | Balcony | Pool
1 bed
1.5 baths
6 guests
Average Price:
$455
35% Cheaper
than normal
AirDNA Score: 30
$255/night
Dog-friendly 1st-Floor Seaside 1BR Cottage | Pool
1 bed
1 bath
4 guests
Average Price:
$400
36% Cheaper
than normal
AirDNA Score: 30
$350/night
Great Oak Bluffs Vacation Getaway!
4 beds
2.5 baths
6 guests
Average Price:
$529
34% Cheaper
than normal
AirDNA Score: 29
$289/night
Lovely 1BR Close to Beach/Golf | Pool | Tennis
1 bed
1.5 baths
4 guests
Average Price:
$495
42% Cheaper
than normal
AirDNA Score: 29
$293/night
Coastal 1BR Island Inn | Patio | Pool
1 bed
1.5 baths
6 guests
Average Price:
$486
40% Cheaper
than normal
AirDNA Score: 29
$209/night
Charming Studio by Beach | Pool | Tennis
studio
1 bath
4 guests
Average Price:
$272
23% Cheaper
than normal
AirDNA Score: 29
$209/night
Coastal Studio Island Inn | Patio | Pool
studio
1 bath
4 guests
Average Price:
$283
26% Cheaper
than normal
AirDNA Score: 29
$285/night
Perfect 2BR Island Inn | Patio | Pool
2 beds
1 bath
4 guests
Average Price:
$258
10% More
than normal
AirDNA Score: 29
$372/night
Comfortable 2BR Island Inn | Pool | Deck
2 beds
2 baths
6 guests
Average Price:
$453
18% Cheaper
than normal
AirDNA Score: 29
$207/night
Dog-friendly Studio By Beach | Pool | Tennis
studio
1 bath
4 guests
Average Price:
$310
33% Cheaper
than normal
AirDNA Score: 28
$450/night
Beach home just 0.8 miles to Farm Neck Golf Club!
3 beds
2 baths
6 guests
Average Price:
$482
7% Cheaper
than normal
AirDNA Score: 25
$318/night
Lovely 1BR Half Mile to Beach | Pool | Tennis
1 bed
1.5 baths
6 guests
Average Price:
$496
36% Cheaper
than normal