The Best Airbnb Deals in
Pittsfield, Vermont

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

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AirDNA Score: 71
$99/night

Peaceful Pittsfield Retreat

1 bed
1 bath
4 guests
Average Price:  
$94
5% More
than normal
AirDNA Score: 65
$1250/night

4-Season Retreat (Pittsfield) near Killington

4 beds
3 baths
12 guests
Average Price:  
$875
43% More
than normal
AirDNA Score: 63
$225/night

Killington area home - 4-seasons & hot tub

3 beds
2.5 baths
15 guests
Average Price:  
$332
32% Cheaper
than normal
AirDNA Score: 63
$645/night

Luxury Heart of VT Green Mountains

4 beds
3.5 baths
8 guests
Average Price:  
$710
9% Cheaper
than normal
AirDNA Score: 62
$313/night

Vermont Friends & Family Home!!! Ski, Hike, Bike

5 beds
2.5 baths
14 guests
Average Price:  
$400
22% Cheaper
than normal
AirDNA Score: 59
$236/night

Clear River Inn - 2 Bedroom Suite

2 beds
1 bath
6 guests
Average Price:  
$392
40% Cheaper
than normal
AirDNA Score: 58
$185/night

A million-dollar view near Killington on 60 acres.

4 beds
1.5 baths
8 guests
Average Price:  
$223
17% Cheaper
than normal
AirDNA Score: 53
$265/night

Four season Killington/Pico area chalet

3 beds
1.5 baths
8 guests
Average Price:  
$411
36% Cheaper
than normal
AirDNA Score: 51
$700/night

Relaxing retreat with lots of land near Killington

4 beds
3 baths
12 guests
Average Price:  
$995
30% Cheaper
than normal
AirDNA Score: 48
$400/night

Killington ski house with amazing mountain views

4 beds
2 baths
8 guests
Average Price:  
$572
30% Cheaper
than normal
AirDNA Score: 48
$450/night

Killington family friendly all season house

5 beds
2 baths
12 guests
Average Price:  
$584
23% Cheaper
than normal
AirDNA Score: 43
$403/night

Silver Spring Chalet Large 4 bedroom, Pittsfield VT, 20 min to Killington Slopes

4 beds
3 baths
11 guests
Average Price:  
$612
34% Cheaper
than normal
AirDNA Score: 38
$400/night

Beautiful Mountain Log Cabin with Scenic Views

3 beds
2 baths
8 guests
Average Price:  
$522
23% Cheaper
than normal
AirDNA Score: 37
$245/night

Green MT Views Min''s away from Killington w Sauna!

4 beds
2.5 baths
10 guests
Average Price:  
$379
35% Cheaper
than normal
AirDNA Score: 32
$92/night

Killington/PICO Ski House Hot Tub & Fast Wifi

3 beds
2 baths
8 guests
Average Price:  
$266
65% Cheaper
than normal
AirDNA Score: 31
$723/night

Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington

3 beds
2 baths
12 guests
Average Price:  
$807
10% Cheaper
than normal
AirDNA Score: 30
$1050/night

Swiss Farm Inn - Killington Area - Sleeps 30

14 beds
14.5 baths
16 guests
Average Price:  
$1316
20% Cheaper
than normal
AirDNA Score: 29
$850/night

Large 5 Bdrm House with Hot Tub

5 beds
3 baths
16 guests
Average Price:  
$907
6% Cheaper
than normal
AirDNA Score: 24
$350/night

GORGEOUS Classic Vermont Ski Chalet With FirePlace

4 beds
2 baths
8 guests
Average Price:  
$649
46% Cheaper
than normal