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
$199/night

Walk to Town, beach and amazing location 113A

2 beds
1.5 baths
4 guests
Average Price:  
$596
67% Cheaper
than normal
AirDNA Score: 79
$199/night

Best location!!! Beach & Town 5min walk 113R

1 bed
1 bath
4 guests
Average Price:  
$392
49% Cheaper
than normal
AirDNA Score: 79
$225/night

Sweet little post and beam

1 bed
1.5 baths
2 guests
Average Price:  
$352
36% Cheaper
than normal
AirDNA Score: 79
$595/night

Victorian Luxury: 1BR+, Driveway, hot tub, patio, grill, in-town

1 bed
1 bath
4 guests
Average Price:  
$543
10% More
than normal
AirDNA Score: 74
$189/night

Stunning private apartment walk to everything!111C

1 bed
1 bath
4 guests
Average Price:  
$359
47% Cheaper
than normal
AirDNA Score: 71
$115/night

Sunny Studio Apartment on Martha''s Vineyard

1 bed
1 bath
2 guests
Average Price:  
$439
74% Cheaper
than normal
AirDNA Score: 71
$179/night

Walk to beach and all Downtown Oak Bluffs !111F

1 bed
1 bath
4 guests
Average Price:  
$350
49% Cheaper
than normal
AirDNA Score: 71
$425/night

Spectacular beach & pool combo; beautiful sunsets!

4 beds
5.5 baths
10 guests
Average Price:  
$833
49% 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:  
$390
23% Cheaper
than normal
AirDNA Score: 67
$245/night

Downtown Oak Bluffs, First Floor Harbor House.

1 bed
1 bath
3 guests
Average Price:  
$514
52% Cheaper
than normal
AirDNA Score: 66
$530/night

Top Cottage

6 beds
3.5 baths
12 guests
Average Price:  
$559
5% Cheaper
than normal
AirDNA Score: 66
$1000/night

NEW 5-bd, 4.5-bth home! Minutes from downtown OB.

5 beds
4.5 baths
12 guests
Average Price:  
$1552
36% Cheaper
than normal
AirDNA Score: 66
$790/night

Historic 1800''s House In Town/Beach

2 beds
2 baths
8 guests
Average Price:  
$1477
47% Cheaper
than normal
AirDNA Score: 65
$350/night

Historic East Chop Beach House

4 beds
2 baths
7 guests
Average Price:  
$521
33% Cheaper
than normal
AirDNA Score: 65
$749/night

Martha''s Vineyard Oak Bluffs Contemporary House

3 beds
2 baths
6 guests
Average Price:  
$761
2% Cheaper
than normal
AirDNA Score: 64
$149/night

Central location for your vacation

2 beds
1 bath
6 guests
Average Price:  
$301
50% Cheaper
than normal
AirDNA Score: 64
$295/night

Downtown Oak Bluffs, 2nd floor Harbor house.

2 beds
1 bath
4 guests
Average Price:  
$538
45% Cheaper
than normal
AirDNA Score: 61
$350/night

The Lighthouse

3 beds
2 baths
9 guests
Average Price:  
$462
24% Cheaper
than normal
AirDNA Score: 61
$1800/night

Private Heated Pool, Wifi, AC, Grill & Firepit

5 beds
4.5 baths
16 guests
Average Price:  
$4083
56% Cheaper
than normal
AirDNA Score: 59
$500/night

Oak Bluffs apartment, walk to town and beach!

2 beds
1 bath
4 guests
Average Price:  
$551
9% Cheaper
than normal
AirDNA Score: 59
$800/night

An Oak Bluffs cottage in town

4 beds
2 baths
8 guests
Average Price:  
$923
13% Cheaper
than normal
AirDNA Score: 58
$700/night

Newly Renovated Walk Town Oak Bluffs 4B/3b AC

4 beds
3 baths
9 guests
Average Price:  
$1042
33% Cheaper
than normal
AirDNA Score: 58
$999/night

CENTRAL AIR!! WALK EVERYWHERE!

5 beds
3 baths
8 guests
Average Price:  
$830
20% More
than normal
AirDNA Score: 57
$190/night

Martha''s Vineyard studio apartment

1 bed
1 bath
2 guests
Average Price:  
$238
20% Cheaper
than normal
AirDNA Score: 56
$375/night

Oak Bluffs Walk to Town

2 beds
2.5 baths
8 guests
Average Price:  
$720
48% Cheaper
than normal
AirDNA Score: 55
$225/night

Mermaid Cottage with hot tub

1 bed
1 bath
4 guests
Average Price:  
$301
25% Cheaper
than normal
AirDNA Score: 51
$150/night

Bright 2-Bedroom Apt near walking & biking trails

2 beds
1 bath
4 guests
Average Price:  
$246
39% Cheaper
than normal
AirDNA Score: 51
$485/night

FABULOUS OCEAN VIEWS-Oak Bluffs Condo Across Beach

2 beds
2 baths
4 guests
Average Price:  
$636
24% Cheaper
than normal
AirDNA Score: 51
$1200/night

NEW Modern Waterfront Beauty! "The Harper House"

4 beds
2.5 baths
8 guests
Average Price:  
$1504
20% 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: 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
$1000/night

Oak Bluff''s Victorian Near Town & Beaches

4 beds
4.5 baths
11 guests
Average Price:  
$1362
27% Cheaper
than normal
AirDNA Score: 47
$750/night

Now booking for Summer 2023! New kitchen & bath!

4 beds
4 baths
9 guests
Average Price:  
$1049
29% Cheaper
than normal
AirDNA Score: 46
$10000/night

The Park Estate: Your Martha''s Vineyard Getaway!

6 beds
5 baths
16 guests
Average Price:  
$8043
24% More
than normal
AirDNA Score: 46
$750/night

Newly renovated, New Pool 2022! Rest, Relax, Renew

4 beds
2.5 baths
8 guests
Average Price:  
$1393
46% Cheaper
than normal
AirDNA Score: 46
$475/night

Classic Vineyard Home In-Town: Best Location Ever!

4 beds
1.5 baths
8 guests
Average Price:  
$533
11% Cheaper
than normal
AirDNA Score: 45
$395/night

Saltbox Cottage in Oak Bluffs

2 beds
1.5 baths
6 guests
Average Price:  
$546
28% Cheaper
than normal
AirDNA Score: 45
$500/night

Martha''s Vineyard Oak Bluffs June July Only

4 beds
2 baths
7 guests
Average Price:  
$589
15% Cheaper
than normal
AirDNA Score: 43
$395/night

Vineyard Social

5 beds
4.5 baths
14 guests
Average Price:  
$722
45% Cheaper
than normal
AirDNA Score: 43
$349/night

Classic yacht

1 bed
0 bath
2 guests
Average Price:  
$295
18% More
than normal
AirDNA Score: 41
$212/night

Martha''s Vineyard house near Lagoon Pond Beach

2 beds
2 baths
4 guests
Average Price:  
$443
52% Cheaper
than normal
AirDNA Score: 40
$500/night

Beautiful home in private setting: Sat to Sat only

3 beds
2.5 baths
6 guests
Average Price:  
$465
8% More
than normal
AirDNA Score: 40
$425/night

Cozy, Clean, Bikes, Kayaks, Lagoon

3 beds
1 bath
7 guests
Average Price:  
$452
6% Cheaper
than normal
AirDNA Score: 39
$880/night

Ploughshare

3 beds
2.5 baths
9 guests
Average Price:  
$909
3% Cheaper
than normal
AirDNA Score: 39
$240/night

Cozy Vacation Getaway On Bike Path

3 beds
1 bath
6 guests
Average Price:  
$379
37% Cheaper
than normal
AirDNA Score: 38
$300/night

One Bed Apartment 0.8 miles to Farm Neck Golf!!

1 bed
1 bath
4 guests
Average Price:  
$445
33% Cheaper
than normal
AirDNA Score: 38
$350/night

The Beach Hive

3 beds
2.5 baths
8 guests
Average Price:  
$520
33% Cheaper
than normal
AirDNA Score: 37
$200/night

Vineyard Hills Suite

1 bed
1 bath
2 guests
Average Price:  
$197
2% More
than normal
AirDNA Score: 37
$513/night

Spectacular Martha''s Vineyard Island Home!

3 beds
2.5 baths
10 guests
Average Price:  
$612
16% Cheaper
than normal
AirDNA Score: 32
$263/night

Cute condo with WiFi, pool & tennis - close to golf & the beach

2 beds
1 bath
6 guests
Average Price:  
$297
11% Cheaper
than normal
AirDNA Score: 29
$325/night

Charming 2 BR Cottage on Brush Pond

2 beds
1 bath
5 guests
Average Price:  
$462
30% Cheaper
than normal
AirDNA Score: 29
$277/night

Comfortable, dog-friendly condo with pool & tennis - perfect location

2 beds
1 bath
4 guests
Average Price:  
$306
9% Cheaper
than normal
AirDNA Score: 28
$450/night

Family home just 0.8 miles to Farm Neck Golf Club!

3 beds
2 baths
6 guests
Average Price:  
$511
12% Cheaper
than normal
AirDNA Score: 27
$200/night

Sweet Second Floor Apartment on Circuit Ave!

1 bed
1 bath
3 guests
Average Price:  
$533
62% Cheaper
than normal
AirDNA Score: 22
$714/night

Great Rental on Martha''s Vineyard - Weekly

4 beds
2 baths
8 guests
Average Price:  
$558
28% More
than normal
AirDNA Score: 22
$1000/night

Harthaven house 2 acres, 3 br 2 ba plus xtra space

3 beds
2 baths
7 guests
Average Price:  
$1011
1% Cheaper
than normal
AirDNA Score: 21
$556/night

Classic, private estate with a large lot, a stone patio & a fireplace!

4 beds
4 baths
8 guests
Average Price:  
$1045
47% Cheaper
than normal
AirDNA Score: 18
$1050/night

Warm, cozy, storybook Cottage near shops & dining

2 beds
1 bath
3 guests
Average Price:  
$1108
5% Cheaper
than normal
AirDNA Score: 16
$450/night

Martha’s Vineyard Peaceful Get Away

2 beds
1.5 baths
4 guests
Average Price:  
$504
11% Cheaper
than normal
AirDNA Score: 15
$320/night

Oak Bluffs Contemporary Summer Home

3 beds
2 baths
6 guests
Average Price:  
$299
7% More
than normal
AirDNA Score: 15
$250/night

Charming four bedroom house in historical district

4 beds
2.5 baths
8 guests
Average Price:  
$516
52% Cheaper
than normal
AirDNA Score: 14
$800/night

Sweet Summer House

4 beds
3 baths
8 guests
Average Price:  
$1495
46% Cheaper
than normal
AirDNA Score: 14
$1500/night

Waterfront Beach Vacation

3 beds
2.5 baths
9 guests
Average Price:  
$1637
8% Cheaper
than normal