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
$217/night

Walk to Town, beach and amazing location 113A

2 beds
1.5 baths
4 guests
Average Price:  
$518
58% Cheaper
than normal
AirDNA Score: 86
$85/night

Lovely 2 BR Oak Bluffs Apartment

2 beds
1 bath
4 guests
Average Price:  
$208
59% Cheaper
than normal
AirDNA Score: 79
$179/night

Stunning. Walk to Beach, Town and Harbor 113B

1 bed
1 bath
2 guests
Average Price:  
$366
51% Cheaper
than normal
AirDNA Score: 79
$245/night

Sweet little post and beam

2 beds
1.5 baths
2 guests
Average Price:  
$384
36% Cheaper
than normal
AirDNA Score: 79
$395/night

Victorian Oasis: Driveway, hot tub, grill & more

1 bed
1 bath
4 guests
Average Price:  
$506
22% Cheaper
than normal
AirDNA Score: 74
$171/night

Beautiful private apartment walk to everything!

1 bed
1 bath
4 guests
Average Price:  
$378
55% Cheaper
than normal
AirDNA Score: 71
$123/night

In-Town Retreat: Deck, Walk to beach, a Gem!

1 bed
1.5 baths
4 guests
Average Price:  
$350
65% Cheaper
than normal
AirDNA Score: 71
$443/night

Spectacular beach & pool combo; beautiful sunsets!

4 beds
5.5 baths
10 guests
Average Price:  
$1013
56% Cheaper
than normal
AirDNA Score: 71
$129/night

Sunny Studio Apartment on Martha''s Vineyard

1 bed
1 bath
2 guests
Average Price:  
$303
57% 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:  
$393
17% Cheaper
than normal
AirDNA Score: 67
$300/night

Downtown Oak Bluffs, First Floor Harbor House.

1 bed
1 bath
3 guests
Average Price:  
$572
48% Cheaper
than normal
AirDNA Score: 66
$199/night

Arrowsmith Cottage-near Eastville Beach-Oak Bluffs

2 beds
1 bath
4 guests
Average Price:  
$400
50% Cheaper
than normal
AirDNA Score: 66
$1050/night

Modern 5-bd, 4.5-bth home. Now booking for 2024!

5 beds
4.5 baths
12 guests
Average Price:  
$1330
21% 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:  
$562
38% Cheaper
than normal
AirDNA Score: 65
$695/night

Martha''s Vineyard Oak Bluffs Contemporary House

3 beds
2 baths
6 guests
Average Price:  
$842
17% Cheaper
than normal
AirDNA Score: 64
$300/night

Downtown Oak Bluffs, 2nd floor Harbor house.

2 beds
1 bath
4 guests
Average Price:  
$599
50% Cheaper
than normal
AirDNA Score: 61
$350/night

The Lighthouse

3 beds
2 baths
9 guests
Average Price:  
$467
25% Cheaper
than normal
AirDNA Score: 59
$800/night

An Oak Bluffs cottage in town

4 beds
2 baths
8 guests
Average Price:  
$855
6% Cheaper
than normal
AirDNA Score: 58
$850/night

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

4 beds
3 baths
9 guests
Average Price:  
$1089
22% Cheaper
than normal
AirDNA Score: 52
$900/night

Oceanview Martha''s Vineyard

4 beds
4.5 baths
9 guests
Average Price:  
$1001
10% Cheaper
than normal
AirDNA Score: 52
$450/night

Oak Bluffs Cottage - Walk to Town & Beach

2 beds
1 bath
4 guests
Average Price:  
$550
18% Cheaper
than normal
AirDNA Score: 51
$450/night

Serenity on Martha''s Vineyard

2 beds
2 baths
5 guests
Average Price:  
$608
26% Cheaper
than normal
AirDNA Score: 51
$1000/night

NEW Modern Waterfront Beauty! "The Harper House"

4 beds
2.5 baths
8 guests
Average Price:  
$2066
52% Cheaper
than normal
AirDNA Score: 50
$419/night

Play, Pace, Peace (and Parking too!)!

5 beds
2 baths
8 guests
Average Price:  
$858
51% Cheaper
than normal
AirDNA Score: 50
$1200/night

Large Modern Home Pool, Hot Tub and Pond Near Town

6 beds
4.5 baths
15 guests
Average Price:  
$2257
47% Cheaper
than normal
AirDNA Score: 47
$1200/night

Martha''s Vineyard Vacation Rental

5 beds
4.5 baths
10 guests
Average Price:  
$1287
7% Cheaper
than normal
AirDNA Score: 47
$765/night

The quintessential MV home. Now booking for 2024!

4 beds
4 baths
9 guests
Average Price:  
$1324
42% Cheaper
than normal
AirDNA Score: 46
$10000/night

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

6 beds
5 baths
16 guests
Average Price:  
$10750
7% Cheaper
than normal
AirDNA Score: 46
$1194/night

Newly renovated! Heated Pool! Firepit! Relax,Renew

4 beds
2.5 baths
9 guests
Average Price:  
$1440
17% Cheaper
than normal
AirDNA Score: 45
$800/night

Ellen''s Cape: Fall Vacay awaits! Booking for 2024!

3 beds
4.5 baths
7 guests
Average Price:  
$754
6% More
than normal
AirDNA Score: 44
$384/night

Breezy Oak Bluffs Condo - Steps to Inkwell Beach!

2 beds
2 baths
4 guests
Average Price:  
$476
19% Cheaper
than normal
AirDNA Score: 43
$495/night

Vineyard Social

5 beds
4.5 baths
14 guests
Average Price:  
$769
36% Cheaper
than normal
AirDNA Score: 41
$225/night

Martha''s Vineyard house near Lagoon Pond Beach

2 beds
2 baths
4 guests
Average Price:  
$539
58% Cheaper
than normal
AirDNA Score: 39
$880/night

Ploughshare

3 beds
2.5 baths
9 guests
Average Price:  
$941
6% Cheaper
than normal
AirDNA Score: 39
$240/night

Cozy Vacation Getaway On Bike Path

3 beds
1 bath
6 guests
Average Price:  
$482
50% Cheaper
than normal
AirDNA Score: 38
$162/night

One Bed Apartment 0.8 miles to Farm Neck Golf!!

1 bed
1 bath
4 guests
Average Price:  
$323
50% Cheaper
than normal
AirDNA Score: 38
$300/night

Bright Modern Stylish House w/3 full bths!

4 beds
3 baths
8 guests
Average Price:  
$378
21% Cheaper
than normal
AirDNA Score: 38
$325/night

The Beach Hive

3 beds
2.5 baths
8 guests
Average Price:  
$500
35% 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
$520/night

Spectacular Martha''s Vineyard Island Home!

3 beds
2.5 baths
10 guests
Average Price:  
$767
32% Cheaper
than normal
AirDNA Score: 32
$170/night

Cute 2BR Island Inn | Patio | Pool

2 beds
1 bath
6 guests
Average Price:  
$261
35% Cheaper
than normal
AirDNA Score: 29
$451/night

Charming 2+ BR Cottage on Brush Pond-

3 beds
1 bath
6 guests
Average Price:  
$491
8% Cheaper
than normal
AirDNA Score: 28
$225/night

Family home just 0.8 miles to Farm Neck Golf Club!

3 beds
2 baths
6 guests
Average Price:  
$522
57% Cheaper
than normal
AirDNA Score: 27
$200/night

Sweet Second Floor Apartment on Circuit Ave!

2 beds
1 bath
4 guests
Average Price:  
$559
64% Cheaper
than normal
AirDNA Score: 23
$887/night

Luxury 5BR | Pool | Fireplace | Balcony

5 beds
4.5 baths
10 guests
Average Price:  
$784
13% More
than normal
AirDNA Score: 23
$105/night

Cozy 3BR | Furnished Deck | Central Location

3 beds
2 baths
6 guests
Average Price:  
$315
67% 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
$361/night

Serene 4BR Dog Friendly | Patio | W/D

4 beds
2 baths
8 guests
Average Price:  
$430
16% Cheaper
than normal
AirDNA Score: 21
$581/night

Spacious 4BR | Dog-friendly | Fenced yard

4 beds
2 baths
10 guests
Average Price:  
$592
2% Cheaper
than normal
AirDNA Score: 18
$1246/night

Classic MVY Cottage, private, in prime location

2 beds
1 bath
3 guests
Average Price:  
$1242
0% 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
$350/night

Oak Bluffs Contemporary Summer Home

3 beds
2 baths
6 guests
Average Price:  
$338
4% More
than normal
AirDNA Score: 15
$250/night

Charming four bedroom house in historical district

4 beds
2.5 baths
4 guests
Average Price:  
$533
53% Cheaper
than normal
AirDNA Score: 15
$500/night

Separate entrance 3 beds, bath and kitchenette

1 bed
1 bath
3 guests
Average Price:  
$378
32% More
than normal
AirDNA Score: 15
$1000/night

Privacy and serenity. An ideal vacation spot

3 beds
2 baths
7 guests
Average Price:  
$932
7% More
than normal
AirDNA Score: 14
$1860/night

Waterfront Beach Vacation

3 beds
2.5 baths
9 guests
Average Price:  
$1948
5% Cheaper
than normal
AirDNA Score: 12
$300/night

Home Away From Home in Martha''s Vineyard

3 beds
3 baths
8 guests
Average Price:  
$373
20% Cheaper
than normal