The Best Airbnb Deals in
Chilmark, Massachusetts

Save money on your trip by finding the biggest discounts for top-rated Airbnb rentals in Chilmark, Massachusetts. Enter your travel dates to find the best deals!

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AirDNA Score: 86
$250/night

Beautiful Guest House in Chilmark

1 bed
1 bath
2 guests
Average Price:  
$297
16% Cheaper
than normal
AirDNA Score: 81
$650/night

The Hidden Getaway

4 beds
2 baths
8 guests
Average Price:  
$650
0% Cheaper
than normal
AirDNA Score: 76
$230/night

Chilmark Gem

1 bed
1 bath
3 guests
Average Price:  
$274
16% Cheaper
than normal
AirDNA Score: 71
$250/night

4-Season Guest House on Historic Chilmark Estate

1 bed
1 bath
2 guests
Average Price:  
$335
25% Cheaper
than normal
AirDNA Score: 58
$500/night

Lookout Cottage

1 bed
1 bath
3 guests
Average Price:  
$634
21% Cheaper
than normal
AirDNA Score: 58
$475/night

Modern Aquinnah home close to the beach- 5 beds

4 beds
2 baths
8 guests
Average Price:  
$530
10% Cheaper
than normal
AirDNA Score: 56
$570/night

Cool, Mid Century House -- Lucy Vincent Beach!

4 beds
3 baths
8 guests
Average Price:  
$1121
49% Cheaper
than normal
AirDNA Score: 53
$928/night

Tucked away on Tea Lane, Chilmark

4 beds
2.5 baths
9 guests
Average Price:  
$878
6% More
than normal
AirDNA Score: 51
$450/night

Spacious, Fully-Equipped Home Near Best MV Beaches

4 beds
3.5 baths
10 guests
Average Price:  
$489
8% Cheaper
than normal
AirDNA Score: 51
$571/night

Quintessential Chilmark Retreat

3 beds
2 baths
8 guests
Average Price:  
$769
26% Cheaper
than normal
AirDNA Score: 51
$300/night

Renovated Barn in Chilmark- 3BR

3 beds
2 baths
6 guests
Average Price:  
$353
15% Cheaper
than normal
AirDNA Score: 50
$715/night

secluded, idyllic Martha''s Vineyard beach house

4 beds
3 baths
8 guests
Average Price:  
$765
7% Cheaper
than normal
AirDNA Score: 45
$315/night

Vintage Chilmark Retreat

3 beds
2 baths
6 guests
Average Price:  
$265
19% More
than normal
AirDNA Score: 44
$520/night

Relax on a Water View Farm

3 beds
1.5 baths
6 guests
Average Price:  
$695
25% Cheaper
than normal
AirDNA Score: 44
$650/night

Comfortable 3BR Home, minutes from Menemsha Harbor

3 beds
2 baths
6 guests
Average Price:  
$838
22% Cheaper
than normal
AirDNA Score: 38
$414/night

Charming Vintage Chilmark Cottage

2 beds
bath
5 guests
Average Price:  
$467
11% Cheaper
than normal
AirDNA Score: 36
$1200/night

Historic Chilmark Farmhouse at the Allen Farm

5 beds
3 baths
10 guests
Average Price:  
$1200
0% Cheaper
than normal
AirDNA Score: 33
$500/night

Contemporary in Chilmark Woods

5 beds
4 baths
14 guests
Average Price:  
$691
28% Cheaper
than normal
AirDNA Score: 33
$375/night

Secluded Chilmark, Martha’s Vineyard, family spot

4 beds
2 baths
8 guests
Average Price:  
$454
17% Cheaper
than normal
AirDNA Score: 31
$650/night

Private, Beautiful Home in Chilmark Woods

3 beds
2 baths
8 guests
Average Price:  
$818
21% Cheaper
than normal
AirDNA Score: 22
$464/night

Beautiful, Historic Farmhouse & Guest House on Chilmark Pond

4 beds
1.5 baths
6 guests
Average Price:  
$669
31% Cheaper
than normal
AirDNA Score: 22
$1025/night

Classic Chilmark Retreat with Water Views

6 beds
3 baths
11 guests
Average Price:  
$779
32% More
than normal
AirDNA Score: 22
$1142/night

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks

4 beds
2 baths
8 guests
Average Price:  
$1362
16% Cheaper
than normal
AirDNA Score: 17
$335/night

Chilmark home with sunset waterviews

3 beds
2 baths
6 guests
Average Price:  
$530
37% Cheaper
than normal
AirDNA Score: 16
$324/night

Chilmark Cape in private wooded setting

4 beds
2 baths
8 guests
Average Price:  
$539
40% Cheaper
than normal
AirDNA Score: 15
$700/night

Privacy on 30 Acres, Walk to Beach

3 beds
1.5 baths
6 guests
Average Price:  
$887
21% Cheaper
than normal