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!

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AirDNA Score: 97
$385/night

Mid-Century Character & Seclusion, Woodstock Vibes

3 beds
1.5 baths
5 guests
Average Price:  
$454
15% Cheaper
than normal
AirDNA Score: 91
$268/night

Red Maple Spa & Studio on the Sawkill Stream

1 bed
1 bath
3 guests
Average Price:  
$289
7% Cheaper
than normal
AirDNA Score: 86
$99/night

Hotel Woodstock - Daisy Suite

1 bed
1 bath
3 guests
Average Price:  
$117
15% Cheaper
than normal
AirDNA Score: 86
$190/night

Woodstock Mountain Cottage

2 beds
1 bath
4 guests
Average Price:  
$222
14% Cheaper
than normal
AirDNA Score: 86
$99/night

Hotel Woodstock - Aster Suite

1 bed
1 bath
2 guests
Average Price:  
$117
15% Cheaper
than normal
AirDNA Score: 86
$105/night

The Yellow Cottage, a blend of village & nature

1 bed
1 bath
2 guests
Average Price:  
$146
28% Cheaper
than normal
AirDNA Score: 86
$135/night

Pick Herbs at a Quirky Stone Cottage with BBQ and Fireplace

studio
1 bath
2 guests
Average Price:  
$150
10% Cheaper
than normal
AirDNA Score: 86
$200/night

Charming Artist Cottage

2 beds
1 bath
4 guests
Average Price:  
$227
12% Cheaper
than normal
AirDNA Score: 86
$275/night

Pet Friendly Cabin Doh-Ray up at 1450 ft

2 beds
1.5 baths
4 guests
Average Price:  
$314
12% Cheaper
than normal
AirDNA Score: 84
$99/night

Hotel Woodstock - Queen Anne’s Lace Suite

1 bed
1 bath
3 guests
Average Price:  
$108
8% Cheaper
than normal
AirDNA Score: 80
$627/night

Woodstock Retreat Dog Friendly Haus

3 beds
2 baths
8 guests
Average Price:  
$601
4% More
than normal
AirDNA Score: 79
$119/night

BOHEMIAN RHAPSODY - Be Here Now

1 bed
1 bath
2 guests
Average Price:  
$150
21% Cheaper
than normal
AirDNA Score: 79
$190/night

Hidden Pines - Downtown Woodstock by Millstream!

1 bed
1 bath
4 guests
Average Price:  
$223
15% Cheaper
than normal
AirDNA Score: 79
$100/night

Rocket Room - Rock Stars Only

1 bed
1 bath
2 guests
Average Price:  
$140
29% Cheaper
than normal
AirDNA Score: 79
$700/night

Modern Woodstock Farmhouse

4 beds
3 baths
8 guests
Average Price:  
$781
10% Cheaper
than normal
AirDNA Score: 79
$124/night

Hotel Woodstock - Iris Suite

1 bed
1 bath
3 guests
Average Price:  
$109
14% More
than normal
AirDNA Score: 79
$176/night

The Carriage House: Garden Apartment

1 bed
1 bath
2 guests
Average Price:  
$165
7% More
than normal
AirDNA Score: 79
$132/night

The Carriage House: Studio

1 bed
1 bath
2 guests
Average Price:  
$140
6% Cheaper
than normal
AirDNA Score: 79
$295/night

Grapevine Cottage

1 bed
1 bath
2 guests
Average Price:  
$295
0% Cheaper
than normal
AirDNA Score: 79
$600/night

Magical Chalet w/ spectacular views

4 beds
3 baths
8 guests
Average Price:  
$946
37% Cheaper
than normal
AirDNA Score: 79
$185/night

Woodstock Home Close to 3 Towns, Hiking and More

2 beds
1 bath
2 guests
Average Price:  
$205
10% Cheaper
than normal
AirDNA Score: 79
$265/night

Sweeping mountain views/3 bedroom house

3 beds
2 baths
5 guests
Average Price:  
$328
19% Cheaper
than normal
AirDNA Score: 77
$532/night

The Woodstock Getaway

5 beds
3 baths
10 guests
Average Price:  
$572
7% Cheaper
than normal
AirDNA Score: 77
$370/night

Fabulous Family House nr Woodstock Center

4 beds
3 baths
8 guests
Average Price:  
$516
28% Cheaper
than normal
AirDNA Score: 77
$319/night

Private Home ~ In Town ~ Hot Tub~Wood Stove ~Quiet

2 beds
1 bath
4 guests
Average Price:  
$353
10% Cheaper
than normal
AirDNA Score: 74
$310/night

Romantic luxury+stream+walk to town=Brook Cottage

2 beds
1 bath
4 guests
Average Price:  
$361
14% Cheaper
than normal
AirDNA Score: 73
$150/night

Woodstock Country Guest Suite

1 bed
1 bath
1 guest
Average Price:  
$179
16% Cheaper
than normal
AirDNA Score: 73
$410/night

Woodstock Modern Gem, Glorious Heated Saline Pool

3 beds
2 baths
6 guests
Average Price:  
$568
28% Cheaper
than normal
AirDNA Score: 72
$233/night

Woodstock Country Home - Relax/ Explore/ Adventure

2 beds
1 bath
4 guests
Average Price:  
$269
13% Cheaper
than normal
AirDNA Score: 71
$295/night

Romantic Woodstock Getaway

1 bed
1 bath
2 guests
Average Price:  
$324
9% Cheaper
than normal
AirDNA Score: 71
$91/night

Melody Inn

studio
1 bath
2 guests
Average Price:  
$124
27% Cheaper
than normal
AirDNA Score: 71
$1000/night

Woodstock Mountain House

3 beds
2 baths
8 guests
Average Price:  
$1075
7% Cheaper
than normal
AirDNA Score: 71
$450/night

Woodstock Mediterranean Retreat: Heated Pool

4 beds
3 baths
9 guests
Average Price:  
$763
41% Cheaper
than normal
AirDNA Score: 71
$295/night

Woodstock Retreat -walk to town

4 beds
3 baths
10 guests
Average Price:  
$568
48% Cheaper
than normal
AirDNA Score: 71
$288/night

Woodstock Historic Artist Estate - The Carriage House

2 beds
1 bath
4 guests
Average Price:  
$281
2% More
than normal
AirDNA Score: 71
$463/night

Woodstock Secluded Close to Town

3 beds
2.5 baths
7 guests
Average Price:  
$522
11% Cheaper
than normal
AirDNA Score: 71
$163/night

Margaret''s Cottage-WoodstockVillage

2 beds
1 bath
4 guests
Average Price:  
$206
21% Cheaper
than normal
AirDNA Score: 71
$300/night

Spectacular Woodstock Location

1 bed
1 bath
2 guests
Average Price:  
$304
1% Cheaper
than normal
AirDNA Score: 71
$470/night

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

3 beds
3 baths
8 guests
Average Price:  
$723
35% Cheaper
than normal
AirDNA Score: 71
$167/night

Woodstock Streamside Cottage

1 bed
1 bath
2 guests
Average Price:  
$215
22% Cheaper
than normal
AirDNA Score: 71
$200/night

Stunning Woodstock 1 BR Hideaway

1 bed
1 bath
2 guests
Average Price:  
$227
12% Cheaper
than normal
AirDNA Score: 71
$101/night

The Mountain View Abode

1 bed
1 bath
4 guests
Average Price:  
$126
20% Cheaper
than normal
AirDNA Score: 71
$200/night

Beautiful and Private Studio Loft in Woodstock Town Center

studio
1 bath
2 guests
Average Price:  
$213
6% Cheaper
than normal
AirDNA Score: 71
$188/night

Famous Architect - Streamside Cottage w/ hot tub

1 bed
1 bath
2 guests
Average Price:  
$263
29% Cheaper
than normal
AirDNA Score: 71
$241/night

1822 Lewis Cottage - Sauna, Jacuzzi, Swimming Hole

2 beds
2 baths
4 guests
Average Price:  
$290
17% Cheaper
than normal
AirDNA Score: 71
$294/night

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

2 beds
1 bath
4 guests
Average Price:  
$346
15% Cheaper
than normal
AirDNA Score: 70
$135/night

Charming & Private Guest Cottage

1 bed
1 bath
3 guests
Average Price:  
$200
32% Cheaper
than normal
AirDNA Score: 70
$130/night

Redbird 1926

1 bed
1 bath
3 guests
Average Price:  
$144
10% Cheaper
than normal
AirDNA Score: 70
$98/night

Hotel Woodstock - Starflower Suite

1 bed
1 bath
3 guests
Average Price:  
$112
12% Cheaper
than normal
AirDNA Score: 69
$366/night

Tannery Brook Cottage

3 beds
2 baths
6 guests
Average Price:  
$395
7% Cheaper
than normal
AirDNA Score: 69
$167/night

Above the Bike Shop

1 bed
1 bath
2 guests
Average Price:  
$189
12% Cheaper
than normal
AirDNA Score: 69
$205/night

Herb Cottage: history•art•woodstove•walk to town!

1 bed
1 bath
2 guests
Average Price:  
$245
16% Cheaper
than normal
AirDNA Score: 69
$247/night

Jewel above the Pub with a view. Walk everywhere!

2 beds
1 bath
4 guests
Average Price:  
$294
16% Cheaper
than normal
AirDNA Score: 67
$449/night

Explore Woodstock from an Exceptional Home

3 beds
2 baths
6 guests
Average Price:  
$532
16% Cheaper
than normal
AirDNA Score: 67
$176/night

Woodstock Carriage House

4 beds
1.5 baths
6 guests
Average Price:  
$368
52% Cheaper
than normal
AirDNA Score: 67
$206/night

Architect''s Farmhouse in Woodstock

4 beds
1.5 baths
8 guests
Average Price:  
$231
11% Cheaper
than normal
AirDNA Score: 65
$170/night

Coziest Cottage

2 beds
1 bath
4 guests
Average Price:  
$270
37% Cheaper
than normal
AirDNA Score: 64
$280/night

2BR* Rental in Woodstock SPA

2 beds
2 baths
4 guests
Average Price:  
$300
7% Cheaper
than normal
AirDNA Score: 64
$288/night

Beautiful & Spacious Woodstock Home w/ Pool

5 beds
3 baths
10 guests
Average Price:  
$461
38% Cheaper
than normal
AirDNA Score: 64
$345/night

Historic 18th-century farmhouse in Woodstock, NY.

4 beds
1.5 baths
8 guests
Average Price:  
$377
8% Cheaper
than normal
AirDNA Score: 64
$290/night

2BR Rental in Woodstock SPA

2 beds
1.5 baths
4 guests
Average Price:  
$313
7% Cheaper
than normal
AirDNA Score: 64
$144/night

chezbevet-country cabin retreat

1 bed
1 bath
4 guests
Average Price:  
$165
13% Cheaper
than normal
AirDNA Score: 64
$300/night

Orange Door Retreat

3 beds
1 bath
6 guests
Average Price:  
$321
7% Cheaper
than normal
AirDNA Score: 63
$620/night

4BR Rental with Private SPA

4 beds
3.5 baths
8 guests
Average Price:  
$651
5% Cheaper
than normal
AirDNA Score: 62
$260/night

2 BR , Fireplace & Hot Tub @ heart of Woodstock

2 beds
1 bath
6 guests
Average Price:  
$302
14% Cheaper
than normal
AirDNA Score: 61
$264/night

Spacious, Private, Close to Town, Work From Home

3 beds
2.5 baths
6 guests
Average Price:  
$429
38% Cheaper
than normal
AirDNA Score: 61
$158/night

Mtn Stream Retreat: rustic elegance•woodstove•view

1 bed
1 bath
2 guests
Average Price:  
$192
18% Cheaper
than normal
AirDNA Score: 59
$262/night

Dove House on Trannery Brook in Woodstock

1 bed
1 bath
2 guests
Average Price:  
$282
7% Cheaper
than normal
AirDNA Score: 56
$326/night

The Cottage in Woodstock

2 beds
1 bath
4 guests
Average Price:  
$503
35% Cheaper
than normal
AirDNA Score: 54
$260/night

Contemporary Cabin With Fireplace

1 bed
1 bath
4 guests
Average Price:  
$277
6% Cheaper
than normal
AirDNA Score: 53
$300/night

Adorable Creek Cottage, Comfortble, Pvt, Near Town

2 beds
2 baths
4 guests
Average Price:  
$347
14% Cheaper
than normal
AirDNA Score: 52
$150/night

Nook above the Pub!

1 bed
1 bath
3 guests
Average Price:  
$213
30% Cheaper
than normal
AirDNA Score: 51
$350/night

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

3 beds
2 baths
6 guests
Average Price:  
$595
41% Cheaper
than normal
AirDNA Score: 51
$995/night

Luxury Retreat in the Catskills

3 beds
2 baths
6 guests
Average Price:  
$1045
5% Cheaper
than normal
AirDNA Score: 50
$133/night

Woodstock Private Suite: Ensuite Bath/Patio

1 bed
1 bath
2 guests
Average Price:  
$166
20% Cheaper
than normal
AirDNA Score: 50
$499/night

Country House in the Hudson Valley near Woodstock

1 bed
1 bath
2 guests
Average Price:  
$189
164% More
than normal
AirDNA Score: 50
$222/night

Teahouse Cottage by the River.

studio
1 bath
4 guests
Average Price:  
$272
18% Cheaper
than normal
AirDNA Score: 50
$244/night

The Tinker Street Retreat!

3 beds
2 baths
6 guests
Average Price:  
$269
9% Cheaper
than normal
AirDNA Score: 46
$270/night

Woodstock Arts and Crafts Gem

2 beds
2 baths
3 guests
Average Price:  
$303
11% Cheaper
than normal
AirDNA Score: 45
$348/night

Woodstock Log Cabin with dedicated workspace

3 beds
3 baths
6 guests
Average Price:  
$405
14% Cheaper
than normal
AirDNA Score: 45
$229/night

Woodstock Paradise with Heated Pool

2 beds
1 bath
3 guests
Average Price:  
$343
33% Cheaper
than normal
AirDNA Score: 45
$353/night

BIG COZY HOME 2 Acres, Pond, Option 1 Br Apt Xtra

5 beds
4 baths
11 guests
Average Price:  
$532
34% Cheaper
than normal
AirDNA Score: 41
$403/night

Woodstock Sanctuary Retreat - walk to town!

2 beds
1 bath
4 guests
Average Price:  
$447
10% Cheaper
than normal
AirDNA Score: 41
$154/night

Woodstock Cottage

1 bed
1 bath
3 guests
Average Price:  
$204
25% Cheaper
than normal
AirDNA Score: 28
$1500/night

Stunning contemporary country house

4 beds
3 baths
6 guests
Average Price:  
$1550
3% Cheaper
than normal
AirDNA Score: 25
$222/night

179 Raycliffe Drive, private road

2 beds
2 baths
4 guests
Average Price:  
$265
16% Cheaper
than normal
AirDNA Score: 21
$495/night

Americana time capsule in Woodstock, NY

1 bed
1 bath
2 guests
Average Price:  
$489
1% More
than normal
AirDNA Score: 14
$425/night

Modern Grey Chalet Woodstock

2 beds
1.5 baths
4 guests
Average Price:  
$502
15% Cheaper
than normal