The Best Airbnb Deals in
Woodstock, New York

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

Search for a city
AirDNA Score: 97
$345/night

Mid-Century Character & Seclusion, Woodstock Vibes

3 beds
1.5 baths
5 guests
Average Price:  
$395
13% Cheaper
than normal
AirDNA Score: 91
$249/night

Red Maple Spa & Studio on the Sawkill Stream

1 bed
1 bath
3 guests
Average Price:  
$305
18% Cheaper
than normal
AirDNA Score: 86
$165/night

The Yellow Cottage, a blend of village & nature

1 bed
1 bath
3 guests
Average Price:  
$157
5% More
than normal
AirDNA Score: 86
$134/night

Hotel Woodstock - Daisy Suite

1 bed
1 bath
3 guests
Average Price:  
$136
1% Cheaper
than normal
AirDNA Score: 86
$200/night

Charming Artist Cottage

2 beds
1 bath
4 guests
Average Price:  
$240
17% Cheaper
than normal
AirDNA Score: 86
$245/night

Pet Friendly Cabin Doh-Ray up at 1450 ft

2 beds
1.5 baths
4 guests
Average Price:  
$313
22% Cheaper
than normal
AirDNA Score: 83
$129/night

Country private apartment suite 1½ mi/ Woodstock

1 bed
1 bath
2 guests
Average Price:  
$130
1% Cheaper
than normal
AirDNA Score: 82
$145/night

Chic Country Apt in Woodstock, NY

1 bed
1 bath
2 guests
Average Price:  
$165
12% Cheaper
than normal
AirDNA Score: 79
$171/night

Woodstock Home Close to 3 Towns, Hiking and More

2 beds
1 bath
2 guests
Average Price:  
$201
15% Cheaper
than normal
AirDNA Score: 79
$198/night

Hidden Pines - Downtown Woodstock by Millstream!

1 bed
1 bath
4 guests
Average Price:  
$222
11% Cheaper
than normal
AirDNA Score: 79
$191/night

Hikers Haven Discount Mountaintop Studio Romantic

1 bed
1 bath
3 guests
Average Price:  
$352
46% Cheaper
than normal
AirDNA Score: 79
$134/night

Hotel Woodstock - Iris Suite

1 bed
1 bath
3 guests
Average Price:  
$126
6% More
than normal
AirDNA Score: 79
$709/night

Magical Chalet w/ spectacular views

4 beds
3 baths
8 guests
Average Price:  
$1165
39% Cheaper
than normal
AirDNA Score: 78
$275/night

Zina''s Cottage in Woodstock NY- river access

studio
1 bath
2 guests
Average Price:  
$281
2% Cheaper
than normal
AirDNA Score: 74
$189/night

Secluded Farmhouse Style, Close to All

1 bed
1 bath
4 guests
Average Price:  
$238
21% Cheaper
than normal
AirDNA Score: 73
$1250/night

Modern Glass House, Minutes to Town

3 beds
3.5 baths
6 guests
Average Price:  
$1526
18% Cheaper
than normal
AirDNA Score: 73
$150/night

Woodstock Country Guest Suite

1 bed
1 bath
1 guest
Average Price:  
$182
18% Cheaper
than normal
AirDNA Score: 73
$380/night

Woodstock Modern Gem, Glorious Heated Saline Pool

3 beds
2 baths
6 guests
Average Price:  
$622
39% Cheaper
than normal
AirDNA Score: 71
$779/night

Luxury Woodstock Retreat- heated pool open 4/11!

6 beds
3 baths
10 guests
Average Price:  
$1010
23% Cheaper
than normal
AirDNA Score: 71
$59/night

Melody Inn

studio
1 bath
2 guests
Average Price:  
$129
54% Cheaper
than normal
AirDNA Score: 71
$675/night

Woodstock Mountain House

2 beds
2 baths
8 guests
Average Price:  
$914
26% Cheaper
than normal
AirDNA Score: 71
$401/night

Woodstock Retreat -walk to town

4 beds
3 baths
10 guests
Average Price:  
$511
22% Cheaper
than normal
AirDNA Score: 71
$450/night

Woodstock Secluded Close to Town

3 beds
2.5 baths
7 guests
Average Price:  
$564
20% Cheaper
than normal
AirDNA Score: 71
$180/night

Margaret''s Cottage-WoodstockVillage

2 beds
1 bath
4 guests
Average Price:  
$198
9% Cheaper
than normal
AirDNA Score: 71
$295/night

Secluded 7acres, Saline Heated Pool, Spa, Stream !

3 beds
3 baths
8 guests
Average Price:  
$750
61% Cheaper
than normal
AirDNA Score: 71
$200/night

Stunning Woodstock 1 BR Hideaway

1 bed
1 bath
3 guests
Average Price:  
$231
13% Cheaper
than normal
AirDNA Score: 71
$180/night

Beautiful and Private Studio Loft in Woodstock Town Center

studio
1 bath
2 guests
Average Price:  
$204
12% Cheaper
than normal
AirDNA Score: 71
$318/night

Woodstock Historic Artist Estate - The Pond House

2 beds
1.5 baths
5 guests
Average Price:  
$593
46% Cheaper
than normal
AirDNA Score: 70
$163/night

Charming & Private Guest Cottage

1 bed
1 bath
3 guests
Average Price:  
$214
24% Cheaper
than normal
AirDNA Score: 70
$100/night

Redbird 1926

1 bed
1 bath
3 guests
Average Price:  
$127
21% Cheaper
than normal
AirDNA Score: 69
$154/night

Above the Bike Shop

1 bed
1 bath
4 guests
Average Price:  
$182
15% Cheaper
than normal
AirDNA Score: 69
$420/night

Tannery Brook Cottage

3 beds
2 baths
6 guests
Average Price:  
$393
7% More
than normal
AirDNA Score: 69
$245/night

Jewel above the Pub with a view. Walk everywhere!

2 beds
1 bath
4 guests
Average Price:  
$294
17% Cheaper
than normal
AirDNA Score: 67
$449/night

Explore Woodstock from an Exceptional Home

3 beds
2 baths
5 guests
Average Price:  
$522
14% Cheaper
than normal
AirDNA Score: 67
$250/night

Woodstock Carriage House

4 beds
1.5 baths
6 guests
Average Price:  
$358
30% Cheaper
than normal
AirDNA Score: 66
$1050/night

Secluded home within walking distance to town

4 beds
3.5 baths
8 guests
Average Price:  
$715
47% More
than normal
AirDNA Score: 65
$90/night

Woodstock Film Fest Apartment

3 beds
1.5 baths
5 guests
Average Price:  
$127
29% Cheaper
than normal
AirDNA Score: 65
$350/night

Heart of Woodstock Village Cottage, fully restored

2 beds
1 bath
4 guests
Average Price:  
$367
5% Cheaper
than normal
AirDNA Score: 64
$360/night

Historic 18th Century Woodstock, NY farmhouse.

4 beds
1.5 baths
8 guests
Average Price:  
$367
2% Cheaper
than normal
AirDNA Score: 64
$169/night

Perfect Woodstock Location- Short Walk to Town

1 bed
1 bath
2 guests
Average Price:  
$172
2% Cheaper
than normal
AirDNA Score: 64
$233/night

Large Woodstock Home w/ Pool in Serene Woodlands.

5 beds
3 baths
10 guests
Average Price:  
$578
60% Cheaper
than normal
AirDNA Score: 63
$325/night

Private & Modern Hot Tub & Fireplace

2 beds
2 baths
6 guests
Average Price:  
$323
1% More
than normal
AirDNA Score: 62
$285/night

2 BR , Fireplace & Hot Tub @ heart of Woodstock

2 beds
1 bath
6 guests
Average Price:  
$289
1% Cheaper
than normal
AirDNA Score: 62
$110/night

Cozy Cabin on the Sawkill Creek

1 bed
1 bath
2 guests
Average Price:  
$96
15% More
than normal
AirDNA Score: 59
$225/night

Dove House on Tannery Brook in Woodstock NY

1 bed
1 bath
2 guests
Average Price:  
$280
20% Cheaper
than normal
AirDNA Score: 59
$750/night

The perfect escape in Woodstock, NY

4 beds
3 baths
8 guests
Average Price:  
$806
7% Cheaper
than normal
AirDNA Score: 58
$362/night

Sunset Mountain Cottage & Pool Privacy Hike Spring

2 beds
1 bath
5 guests
Average Price:  
$470
23% Cheaper
than normal
AirDNA Score: 57
$399/night

DIVINE HOT TUB SUITE in VILLAGE of Woodstock

2 beds
2 baths
4 guests
Average Price:  
$420
5% Cheaper
than normal
AirDNA Score: 56
$650/night

"Boulders Gate" Woodstock retreat with saline pool

4 beds
2 baths
8 guests
Average Price:  
$687
5% Cheaper
than normal
AirDNA Score: 56
$146/night

Gorgeous Private Modern Cottage, Tranquil & Clean

1 bed
1 bath
4 guests
Average Price:  
$179
18% Cheaper
than normal
AirDNA Score: 53
$299/night

Adorable Creek Cottage, Comfortble, Pvt, Near Town

2 beds
2 baths
4 guests
Average Price:  
$351
15% Cheaper
than normal
AirDNA Score: 52
$165/night

Brigadoon--Magical 3BR Farmhouse in Woodstock

3 beds
2.5 baths
6 guests
Average Price:  
$344
52% Cheaper
than normal
AirDNA Score: 52
$173/night

Nook above the Pub!

1 bed
1 bath
4 guests
Average Price:  
$207
16% Cheaper
than normal
AirDNA Score: 52
$369/night

Village Carriage House w/Secret Garden

2 beds
2 baths
4 guests
Average Price:  
$407
9% Cheaper
than normal
AirDNA Score: 52
$1000/night

Idyllic mountain retreat

4 beds
2 baths
6 guests
Average Price:  
$1033
3% Cheaper
than normal
AirDNA Score: 51
$995/night

Luxury Retreat in the Catskills

3 beds
2 baths
6 guests
Average Price:  
$1104
10% Cheaper
than normal
AirDNA Score: 51
$425/night

COUNTRY HOME Fireplace, 1 mi. to Town, Fenced Yard

3 beds
2 baths
6 guests
Average Price:  
$528
20% Cheaper
than normal
AirDNA Score: 50
$225/night

Teahouse Cottage by the River.

studio
1 bath
4 guests
Average Price:  
$247
9% Cheaper
than normal
AirDNA Score: 50
$140/night

Country House in the Hudson Valley near Woodstock

1 bed
1 bath
2 guests
Average Price:  
$171
18% Cheaper
than normal
AirDNA Score: 50
$238/night

The Tinker Street Retreat!

3 beds
2 baths
6 guests
Average Price:  
$291
18% Cheaper
than normal
AirDNA Score: 50
$136/night

Woodstock Private Suite: Ensuite Bath/Patio

1 bed
1 bath
2 guests
Average Price:  
$168
19% Cheaper
than normal
AirDNA Score: 46
$290/night

Woodstock Arts and Crafts Gem

2 beds
2 baths
3 guests
Average Price:  
$299
3% Cheaper
than normal
AirDNA Score: 45
$400/night

BIG HOME w. Pond, Backyard, Opt 1 Br Apt Xtra

5 beds
4 baths
11 guests
Average Price:  
$504
21% Cheaper
than normal
AirDNA Score: 45
$275/night

Hudson Valley Oasis with in-ground pool.

4 beds
2.5 baths
6 guests
Average Price:  
$499
45% Cheaper
than normal
AirDNA Score: 43
$185/night

''Casa Reál'' ~ Expansive Woodstock House w/ Hot Tub

4 beds
4 baths
8 guests
Average Price:  
$603
69% Cheaper
than normal
AirDNA Score: 43
$949/night

Wonderful family compound, NEW hot tub, stream

5 beds
4.5 baths
10 guests
Average Price:  
$918
3% More
than normal
AirDNA Score: 43
$180/night

Mothership B&B

1 bed
1 bath
2 guests
Average Price:  
$167
8% More
than normal
AirDNA Score: 41
$400/night

Woodstock Sanctuary Retreat - walk to town!

2 beds
1 bath
4 guests
Average Price:  
$541
26% Cheaper
than normal
AirDNA Score: 41
$135/night

Woodstock Cottage

1 bed
1 bath
3 guests
Average Price:  
$207
35% Cheaper
than normal
AirDNA Score: 25
$222/night

179 Raycliffe Drive, private road

2 beds
2 baths
4 guests
Average Price:  
$257
14% Cheaper
than normal
AirDNA Score: 19
$853/night

The Croft at Woodstock Way Hotel NO CAR NEEDED

2 beds
1.5 baths
4 guests
Average Price:  
$821
4% More
than normal
AirDNA Score: 14
$425/night

Modern Grey Chalet Woodstock

2 beds
1.5 baths
4 guests
Average Price:  
$503
16% Cheaper
than normal