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!

Search for a city
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

East Chop Cottage

1 bed
0 bath
2 guests
Average Price:  
$380
12% More
than normal
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

The Lighthouse

3 beds
2 baths
9 guests
Average Price:  
$452
23% Cheaper
than normal
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

Nolan''sland

6 beds
2 baths
10 guests
Average Price:  
$899
6% More
than normal
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

Ploughshare

3 beds
2.5 baths
9 guests
Average Price:  
$882
13% Cheaper
than normal
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