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

Quiet Hide Away

1 bed
1 bath
2 guests
Average Price:  
$336
18% Cheaper
than normal
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

East Chop Cottage

1 bed
0 bath
2 guests
Average Price:  
$426
26% Cheaper
than normal
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

The Lighthouse

3 beds
2 baths
9 guests
Average Price:  
$460
18% Cheaper
than normal
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

Robin''s Nest

3 beds
1.5 baths
7 guests
Average Price:  
$550
27% Cheaper
than normal
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

Nolan''sland

6 beds
2 baths
10 guests
Average Price:  
$1080
12% Cheaper
than normal
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

Ploughshare

3 beds
2.5 baths
9 guests
Average Price:  
$937
6% Cheaper
than normal
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

Vineyard Hills Suite

1 bed
1 bath
2 guests
Average Price:  
$197
52% More
than normal
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