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
$140/night
Lovely 2 BR Oak Bluffs Apartment
2 beds
1 bath
4 guests
Average Price:
$197
29% Cheaper
than normal
AirDNA Score: 79
$300/night
Sweet little post and beam
1 bed
1.5 baths
2 guests
Average Price:
$293
2% More
than normal
AirDNA Score: 79
$179/night
Walk to beach and all Oak bluffs has to offer!111D
1 bed
1 bath
4 guests
Average Price:
$439
59% Cheaper
than normal
AirDNA Score: 79
$465/night
OB-Downstairs · Lux 1BR+: Driveway, hot tub, patio, grill, in-town
1 bed
1 bath
4 guests
Average Price:
$710
35% Cheaper
than normal
AirDNA Score: 79
$169/night
Stunning. Walk to Beach, Town and Harbor 113B
1 bed
1 bath
2 guests
Average Price:
$315
46% Cheaper
than normal
AirDNA Score: 79
$180/night
Best location!!! Beach & Town 5min walk 113R
1 bed
1 bath
4 guests
Average Price:
$401
55% Cheaper
than normal
AirDNA Score: 74
$169/night
Stunning private apartment walk to everything!111C
1 bed
1 bath
4 guests
Average Price:
$429
61% Cheaper
than normal
AirDNA Score: 73
$475/night
REMODELED Vineyard cottage. 10 min walk to OB!
3 beds
2.5 baths
7 guests
Average Price:
$807
41% Cheaper
than normal
AirDNA Score: 71
$215/night
Studio apt in newly built barn
studio
1 bath
3 guests
Average Price:
$243
12% Cheaper
than normal
AirDNA Score: 71
$199/night
Stroll to the best Oak Bluffs has to offer!111E
1 bed
1 bath
4 guests
Average Price:
$410
51% Cheaper
than normal
AirDNA Score: 71
$145/night
OB-Upstairs · Oasis in town: Comfie, Deck, Walk to beach, a Gem
1 bed
1.5 baths
4 guests
Average Price:
$349
58% Cheaper
than normal
AirDNA Score: 69
$350/night
Charming water-front cottage on Martha''s Vineyard!
1 bed
1 bath
2 guests
Average Price:
$410
15% Cheaper
than normal
AirDNA Score: 67
$575/night
Downtown Oak Bluffs, First Floor Harbor House.
1 bed
1 bath
3 guests
Average Price:
$412
40% More
than normal
AirDNA Score: 66
$293/night
Arrowsmith Cottage - Oak Bluffs, Martha''s Vineyard
2 beds
1 bath
4 guests
Average Price:
$346
15% Cheaper
than normal
AirDNA Score: 65
$425/night
AirDNA Score: 65
$350/night
Historic East Chop Beach House
4 beds
2 baths
7 guests
Average Price:
$399
12% Cheaper
than normal
AirDNA Score: 65
$495/night
Vineyard Stroll
3 beds
2.5 baths
8 guests
Average Price:
$830
40% Cheaper
than normal
AirDNA Score: 64
$375/night
WATERFRONT PENTHOUSE OAK BLUFFS
studio
1 bath
2 guests
Average Price:
$379
1% Cheaper
than normal
AirDNA Score: 64
$475/night
1.5 Miles to Town and Beach! 2BR/2BA Sleeps 4.
2 beds
2 baths
4 guests
Average Price:
$633
25% Cheaper
than normal
AirDNA Score: 64
$650/night
Downtown Oak Bluffs, 2nd floor Harbor house.
2 beds
1 bath
4 guests
Average Price:
$499
30% More
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:
$815
17% Cheaper
than normal
AirDNA Score: 61
$350/night
AirDNA Score: 61
$300/night
Sea View Waterfront Apartment
1 bed
1 bath
3 guests
Average Price:
$335
10% Cheaper
than normal
AirDNA Score: 59
$281/night
Dog-friendly condo with pool, tennis courts, & picnic area - close to beach
studio
1 bath
4 guests
Average Price:
$226
24% More
than normal
AirDNA Score: 59
$287/night
Dog-friendly studio with shared pool, on-site tennis courts, & prime location
studio
1 bath
4 guests
Average Price:
$242
19% More
than normal
AirDNA Score: 59
$353/night
Dog-friendly condo with WiFi & pool - explore the parks & hit the beach
1 bed
1 bath
4 guests
Average Price:
$258
37% More
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:
$2184
1% More
than normal
AirDNA Score: 58
$279/night
Romance awaits at this condo near the shore with WiFi, pool & tennis courts
studio
1 bath
2 guests
Average Price:
$225
24% More
than normal
AirDNA Score: 58
$525/night
impeccable cottage STEPS to downtown OB & beach!
3 beds
1 bath
7 guests
Average Price:
$537
2% Cheaper
than normal
AirDNA Score: 58
$487/night
Bright old-world cottage w/ two porches & large yard - walk to town/beaches!
3 beds
2.5 baths
6 guests
Average Price:
$468
4% More
than normal
AirDNA Score: 58
$700/night
Newly Renovated Walk Town Oak Bluffs 4B/3b AC
4 beds
3 baths
9 guests
Average Price:
$993
30% Cheaper
than normal
AirDNA Score: 58
$599/night
CENTRAL AIR!! WALK EVERYWHERE!
5 beds
3 baths
8 guests
Average Price:
$815
27% Cheaper
than normal
AirDNA Score: 58
$428/night
Beautiful Home in Great Location
3 beds
2 baths
6 guests
Average Price:
$446
4% Cheaper
than normal
AirDNA Score: 58
$422/night
Enjoy tennis courts and a swimming pool - close to beaches, golf, & town
1 bed
1.5 baths
6 guests
Average Price:
$287
47% More
than normal
AirDNA Score: 58
$411/night
Charming suite with WiFi, pool & tennis courts - 1/2 mile to the beach
1 bed
1.5 baths
6 guests
Average Price:
$290
42% More
than normal
AirDNA Score: 58
$306/night
Charming studio for two with pool & tennis - close to beaches & town
studio
1 bath
4 guests
Average Price:
$215
42% More
than normal
AirDNA Score: 58
$294/night
Comfy studio with WiFi, pool, & tennis court - near the beach, dogs OK
studio
1 bath
4 guests
Average Price:
$207
42% More
than normal
AirDNA Score: 57
$516/night
Dog-friendly townhouse with pool, tennis & more - easy walk to the beach
2 beds
2 baths
6 guests
Average Price:
$356
45% More
than normal
AirDNA Score: 57
$287/night
Dog-friendly studio condo with pool & tennis - close to beaches and golf
studio
1 bath
4 guests
Average Price:
$192
49% More
than normal
AirDNA Score: 57
$529/night
Traditional Martha''s Vineyard Home w/ Porch & Yard
4 beds
3 baths
9 guests
Average Price:
$742
29% Cheaper
than normal
AirDNA Score: 56
$395/night
Oak Bluffs Walk to Town
2 beds
2.5 baths
8 guests
Average Price:
$760
48% Cheaper
than normal
AirDNA Score: 55
$595/night
Renovated 3 bed, 2 1/2 bath w/finished basement
3 beds
2.5 baths
9 guests
Average Price:
$716
17% Cheaper
than normal
AirDNA Score: 54
$300/night
Oak Bluffs near beaches & town, A/C,Jacuzzi,kayaks
4 beds
2.5 baths
10 guests
Average Price:
$479
37% Cheaper
than normal
AirDNA Score: 52
$565/night
Adorable cottage with access to a pool, tennis courts, & picnic area
2 beds
2 baths
6 guests
Average Price:
$396
43% More
than normal
AirDNA Score: 52
$900/night
Oceanview Martha''s Vineyard
4 beds
4.5 baths
9 guests
Average Price:
$1038
13% Cheaper
than normal
AirDNA Score: 52
$1300/night
East Chop Waterview Farmhouse/ Sanitary and Serene
6 beds
4.5 baths
15 guests
Average Price:
$1067
22% More
than normal
AirDNA Score: 51
$1120/night
The Island Collection MV: Seascape
7 beds
4 baths
14 guests
Average Price:
$1859
40% Cheaper
than normal
AirDNA Score: 51
$950/night
AirDNA Score: 51
$1150/night
NEW Modern Waterfront Beauty! "The Harper House"
4 beds
2.5 baths
8 guests
Average Price:
$1247
8% Cheaper
than normal
AirDNA Score: 50
$699/night
Play, Pace, Peace (and Parking too!)!
5 beds
2 baths
8 guests
Average Price:
$873
20% Cheaper
than normal
AirDNA Score: 50
$1500/night
Large Vineyard Home w/Pond, Hot Tub Sleeps 16+
6 beds
4.5 baths
16 guests
Average Price:
$1249
20% More
than normal
AirDNA Score: 47
$785/night
Martha''s Vineyard Vacation Rental
5 beds
4.5 baths
10 guests
Average Price:
$854
8% Cheaper
than normal
AirDNA Score: 47
$750/night
Oak Bluff''s Victorian Near Town & Beaches
4 beds
4.5 baths
11 guests
Average Price:
$1081
31% Cheaper
than normal
AirDNA Score: 47
$675/night
Prime June 2022 week available! New kitchen & bath
4 beds
4 baths
8 guests
Average Price:
$990
32% Cheaper
than normal
AirDNA Score: 46
$6000/night
The Park Estate: Your Martha''s Vineyard Getaway!
6 beds
5 baths
16 guests
Average Price:
$5750
4% More
than normal
AirDNA Score: 46
$695/night
PRIVATE WATER ACCESS ON FARM NECK GOLF COURSE, A/C
3 beds
2.5 baths
7 guests
Average Price:
$672
3% More
than normal
AirDNA Score: 46
$975/night
Villa Rose | Rest, Relax & Renew!
4 beds
2.5 baths
8 guests
Average Price:
$906
8% More
than normal
AirDNA Score: 46
$450/night
Classic Vineyard Home In-Town: Best Location Ever!
4 beds
1.5 baths
8 guests
Average Price:
$477
6% Cheaper
than normal
AirDNA Score: 46
$362/night
Lakefront Cottage with a Deck, Free WiFi, Gas Grill - Close to Ferries & Beaches
2 beds
1 bath
4 guests
Average Price:
$478
24% Cheaper
than normal
AirDNA Score: 45
$500/night
Newly Renovated Home: Oak Bluffs
4 beds
3 baths
10 guests
Average Price:
$625
20% Cheaper
than normal
AirDNA Score: 44
$250/night
September openings available!
3 beds
2.5 baths
6 guests
Average Price:
$431
42% Cheaper
than normal
AirDNA Score: 43
$542/night
MAGICAL & PET FRIENDLY CLOSE TO TOWN/HARBOR/BEACH
5 beds
2 baths
8 guests
Average Price:
$619
12% Cheaper
than normal
AirDNA Score: 43
$495/night
Vineyard Social
5 beds
4.5 baths
14 guests
Average Price:
$704
30% Cheaper
than normal
AirDNA Score: 43
$349/night
Classic yacht for sale
1 bed
0 bath
2 guests
Average Price:
$267
31% More
than normal
AirDNA Score: 40
$350/night
Cozy, Clean, Bikes, Kayaks, Lagoon
3 beds
1 bath
7 guests
Average Price:
$393
11% Cheaper
than normal
AirDNA Score: 39
$770/night
AirDNA Score: 39
$695/night
East Chop Charmer-a/c, big yard, beach, sunsets!
3 beds
2 baths
9 guests
Average Price:
$751
7% Cheaper
than normal
AirDNA Score: 39
$624/night
Charming, Dog-Friendly House with Lots of Entertainment & Gourmet Kitchen
3 beds
2 baths
6 guests
Average Price:
$606
3% More
than normal
AirDNA Score: 39
$250/night
Cozy Vacation Getaway On Bike Path
3 beds
1 bath
6 guests
Average Price:
$319
22% Cheaper
than normal
AirDNA Score: 38
$375/night
One Bed Apartment 0.8 miles to Farm Neck Golf!!
1 bed
1 bath
4 guests
Average Price:
$359
4% More
than normal
AirDNA Score: 38
$300/night
Low Exposure- 5BD on Quiet Street Steps from Beach
5 beds
2 baths
10 guests
Average Price:
$545
45% Cheaper
than normal
AirDNA Score: 38
$313/night
Cozy, dog-friendly condo by the sea with pool, tennis, picnic area
studio
1 bath
4 guests
Average Price:
$242
29% More
than normal
AirDNA Score: 38
$332/night
Cozy condo near the beach with WiFi, pool, tennis, grills, & more
1 bed
1 bath
2 guests
Average Price:
$255
30% More
than normal
AirDNA Score: 37
$185/night
Vineyard Hills Suite
1 bed
1 bath
2 guests
Average Price:
$197
6% Cheaper
than normal
AirDNA Score: 37
$260/night
Oak Bluffs Cottage
3 beds
2 baths
5 guests
Average Price:
$355
27% Cheaper
than normal
AirDNA Score: 37
$423/night
Spectacular Martha''s Vineyard Island Home!
3 beds
2.5 baths
10 guests
Average Price:
$671
37% Cheaper
than normal
AirDNA Score: 37
$521/night
Renovated townhome with pool & 3 tennis courts - golfing & beaches nearby
2 beds
2 baths
6 guests
Average Price:
$390
34% More
than normal
AirDNA Score: 37
$464/night
Charming townhouse with deck, pool & on-site tennis - walk to the beach
2 beds
2 baths
6 guests
Average Price:
$388
20% More
than normal
AirDNA Score: 37
$650/night
Lovely 4 BR house steps from beach
4 beds
2 baths
7 guests
Average Price:
$669
3% Cheaper
than normal
AirDNA Score: 35
$450/night
Relaxing, spacious retreat- seconds from water
4 beds
3 baths
8 guests
Average Price:
$540
17% Cheaper
than normal
AirDNA Score: 33
$601/night
Charming Cottage with Deck and Playroom One Mile from Beach
4 beds
2 baths
8 guests
Average Price:
$547
10% More
than normal
AirDNA Score: 32
$302/night
Seaside suite with tennis courts and a pool, perfect for romantic getaways
studio
1 bath
4 guests
Average Price:
$213
42% More
than normal
AirDNA Score: 32
$451/night
Stylish townhouse 1/2 mile from the beach - tennis courts & pool on-site
2 beds
1.5 baths
6 guests
Average Price:
$317
42% More
than normal
AirDNA Score: 32
$356/night
Cute condo with WiFi, pool & tennis - close to golf & the beach
2 beds
1 bath
6 guests
Average Price:
$280
27% More
than normal
AirDNA Score: 31
$306/night
Charming studio with WiFi, pool, & tennis courts - close to beaches & golf
studio
1 bath
2 guests
Average Price:
$236
30% More
than normal
AirDNA Score: 31
$468/night
Cozy townhouse with WiFi, pool, tennis & great location close to the beach
2 beds
1.5 baths
6 guests
Average Price:
$323
45% More
than normal
AirDNA Score: 31
$296/night
Dog-friendly condo with pool & tennis - close to beaches, golf, & parks
studio
1 bath
4 guests
Average Price:
$210
41% More
than normal
AirDNA Score: 31
$433/night
Fun, Family, Vineyard Getaway
4 beds
2 baths
8 guests
Average Price:
$521
17% Cheaper
than normal
AirDNA Score: 30
$303/night
Welcoming condo with WiFi, pool, & tennis courts - golf & beaches nearby
studio
1 bath
4 guests
Average Price:
$230
32% More
than normal
AirDNA Score: 30
$467/night
Superb townhouse close to golf & the beach - deck, tennis, & pool
2 beds
1.5 baths
6 guests
Average Price:
$326
43% More
than normal
AirDNA Score: 30
$352/night
Dog-friendly first-floor seaside cottage with WiFi, pool, & tennis courts
1 bed
1 bath
2 guests
Average Price:
$275
28% More
than normal
AirDNA Score: 30
$436/night
Dog-friendly condo suite with pool, tennis, & picnic area - close to beach
1 bed
1.5 baths
6 guests
Average Price:
$314
39% More
than normal
AirDNA Score: 29
$401/night
Lovely condo suite, close to golfing & the beach - pool & home comforts
1 bed
1.5 baths
4 guests
Average Price:
$346
16% More
than normal
AirDNA Score: 29
$432/night
Coastal getaway with pool & tennis courts - 1/2 mile from beach, dogs OK
1 bed
1.5 baths
6 guests
Average Price:
$289
49% More
than normal
AirDNA Score: 29
$550/night
Family friendly home w/ ocean views, pool table, full kitchen, & gas fireplace
4 beds
3 baths
8 guests
Average Price:
$706
22% Cheaper
than normal
AirDNA Score: 29
$325/night
Charming 2 BR Cottage on Brush Pond
2 beds
1 bath
5 guests
Average Price:
$525
38% Cheaper
than normal
AirDNA Score: 29
$306/night
Dog-friendly condo with shared pool & tennis - close to golf & beach
studio
1 bath
4 guests
Average Price:
$211
45% More
than normal
AirDNA Score: 29
$368/night
Comfortable, dog-friendly condo with pool & tennis - perfect location
2 beds
1 bath
6 guests
Average Price:
$257
43% More
than normal
AirDNA Score: 29
$508/night
Comfortable townhouse close to town & the beach with outdoor pool & tennis
2 beds
2 baths
6 guests
Average Price:
$361
41% More
than normal
AirDNA Score: 29
$290/night
Charming studio condo with pool & tennis - easy access to the beach
studio
1 bath
4 guests
Average Price:
$210
38% More
than normal