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
$345/night

Mid-Century Character & Seclusion, Woodstock Vibes

3 beds
1.5 baths
5 guests
Average Price:  
$425
19% Cheaper
than normal
AirDNA Score: 91
$245/night

Red Maple Spa & Studio on the Sawkill Stream

1 bed
1 bath
3 guests
Average Price:  
$290
16% Cheaper
than normal
AirDNA Score: 86
$89/night

Hotel Woodstock - Tiger Lily Suite

1 bed
1 bath
4 guests
Average Price:  
$116
23% Cheaper
than normal
AirDNA Score: 86
$150/night

Woodstock Cabin 3 Miles from Town

studio
1 bath
2 guests
Average Price:  
$153
2% Cheaper
than normal
AirDNA Score: 86
$200/night

Woodstock Mountain Cottage

2 beds
1 bath
4 guests
Average Price:  
$222
10% Cheaper
than normal
AirDNA Score: 86
$89/night

Hotel Woodstock - Aster Suite

1 bed
1 bath
2 guests
Average Price:  
$120
26% Cheaper
than normal
AirDNA Score: 86
$89/night

Hotel Woodstock - Daisy Suite

1 bed
1 bath
3 guests
Average Price:  
$116
23% Cheaper
than normal
AirDNA Score: 86
$190/night

Byrdcliffe Artist Studio (27.1-1-70)

studio
1 bath
4 guests
Average Price:  
$190
0% Cheaper
than normal
AirDNA Score: 79
$175/night

Chestnut Hill Hideaway

1 bed
1 bath
2 guests
Average Price:  
$131
34% More
than normal
AirDNA Score: 79
$289/night

Cozy Escape in Woodstock

3 beds
3 baths
8 guests
Average Price:  
$416
31% Cheaper
than normal
AirDNA Score: 79
$89/night

Hotel Woodstock - Iris Suite

1 bed
1 bath
3 guests
Average Price:  
$107
17% Cheaper
than normal
AirDNA Score: 79
$150/night

Outdoor shower. Secluded but walk to restaurants

3 beds
2 baths
4 guests
Average Price:  
$250
40% Cheaper
than normal
AirDNA Score: 79
$245/night

Luxury+firepit+stream+walk/town=Brook Cottage Too

1 bed
1 bath
2 guests
Average Price:  
$294
17% 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
$89/night

Hotel Woodstock - Sunflower Loft Suite

1 bed
1 bath
6 guests
Average Price:  
$117
24% Cheaper
than normal
AirDNA Score: 79
$100/night

The Carriage House: Garden Apartment

1 bed
1 bath
2 guests
Average Price:  
$165
39% Cheaper
than normal
AirDNA Score: 79
$199/night

In town gem. Walk to restaurants. Backyard brook

3 beds
2 baths
9 guests
Average Price:  
$323
38% Cheaper
than normal
AirDNA Score: 79
$295/night

Grapevine Cottage

1 bed
1 bath
2 guests
Average Price:  
$294
0% Cheaper
than normal
AirDNA Score: 79
$269/night

Hikers Haven Romantic Studio w/pool & mtn views

1 bed
1 bath
3 guests
Average Price:  
$330
18% Cheaper
than normal
AirDNA Score: 79
$100/night

Rocket Room - Rock Stars Only

1 bed
1 bath
2 guests
Average Price:  
$137
27% Cheaper
than normal
AirDNA Score: 79
$150/night

Woodstock Haven

2 beds
1 bath
6 guests
Average Price:  
$152
1% Cheaper
than normal
AirDNA Score: 79
$265/night

Marigold - Stream side Cabin W/Hot Tub & Fireplace

1 bed
1.5 baths
4 guests
Average Price:  
$292
9% Cheaper
than normal
AirDNA Score: 79
$155/night

Top of the Hill

1 bed
1 bath
2 guests
Average Price:  
$186
17% Cheaper
than normal
AirDNA Score: 79
$110/night

BOHEMIAN RHAPSODY - Be Here Now

1 bed
1 bath
2 guests
Average Price:  
$153
28% Cheaper
than normal
AirDNA Score: 79
$275/night

Sweeping mountain views/3 bedroom house

3 beds
2 baths
5 guests
Average Price:  
$321
14% Cheaper
than normal
AirDNA Score: 79
$89/night

Hotel Woodstock - Dandelion Suite

1 bed
1 bath
4 guests
Average Price:  
$107
17% Cheaper
than normal
AirDNA Score: 77
$125/night

Byrdcliffe Retreat Woodstock, NY

1 bed
1 bath
1 guest
Average Price:  
$143
13% Cheaper
than normal
AirDNA Score: 77
$399/night

Fabulous Family House nr Woodstock Center

4 beds
3 baths
8 guests
Average Price:  
$497
20% Cheaper
than normal
AirDNA Score: 77
$255/night

Entire house ~ in Town ~ Hot Tub ~ Quiet Location

2 beds
1 bath
4 guests
Average Price:  
$354
28% Cheaper
than normal
AirDNA Score: 77
$125/night

The Woodstock Suite

studio
1 bath
2 guests
Average Price:  
$137
9% Cheaper
than normal
AirDNA Score: 77
$188/night

Visit Woodstock from a Radiant 1940s Cottage

1 bed
1 bath
2 guests
Average Price:  
$228
18% Cheaper
than normal
AirDNA Score: 74
$199/night

Secluded Farmhouse Style, Close to All

1 bed
1 bath
4 guests
Average Price:  
$239
17% Cheaper
than normal
AirDNA Score: 73
$150/night

Woodstock Country Guest Suite

1 bed
1 bath
1 guest
Average Price:  
$180
17% Cheaper
than normal
AirDNA Score: 73
$1750/night

Modern Glass House, Minutes to Town

3 beds
3.5 baths
6 guests
Average Price:  
$1407
24% More
than normal
AirDNA Score: 73
$525/night

Woodstock Modern Gem, Glorious Heated Saline Pool

3 beds
2 baths
6 guests
Average Price:  
$567
7% Cheaper
than normal
AirDNA Score: 71
$900/night

Woodstock Mountain House

3 beds
2 baths
8 guests
Average Price:  
$809
11% More
than normal
AirDNA Score: 71
$89/night

Melody Inn

studio
1 bath
2 guests
Average Price:  
$126
29% Cheaper
than normal
AirDNA Score: 71
$225/night

Famous Architect - Streamside Cottage w/ hot tub

1 bed
1 bath
2 guests
Average Price:  
$268
16% Cheaper
than normal
AirDNA Score: 71
$445/night

Woodstock Retreat -walk to town

4 beds
3 baths
10 guests
Average Price:  
$540
18% Cheaper
than normal
AirDNA Score: 71
$675/night

Woodstock Mediterranean Retreat: Heated Pool

4 beds
3 baths
9 guests
Average Price:  
$753
10% Cheaper
than normal
AirDNA Score: 71
$799/night

Luxury Woodstock Family Retreat with pool/hot tub

6 beds
3 baths
10 guests
Average Price:  
$985
19% Cheaper
than normal
AirDNA Score: 71
$160/night

Margaret''s Cottage-WoodstockVillage

2 beds
1 bath
4 guests
Average Price:  
$204
22% Cheaper
than normal
AirDNA Score: 71
$300/night

Spectacular Woodstock Location

1 bed
1 bath
2 guests
Average Price:  
$300
0% Cheaper
than normal
AirDNA Score: 71
$200/night

Beautiful and Private Studio Loft in Woodstock Town Center

studio
1 bath
2 guests
Average Price:  
$208
4% Cheaper
than normal
AirDNA Score: 71
$241/night

1822 farmhouse-SaunaJacuzziSwimhole

2 beds
2 baths
4 guests
Average Price:  
$288
16% Cheaper
than normal
AirDNA Score: 71
$270/night

MountainView, HotTub, Sauna, 2 Fireplcs, fire pit

2 beds
1 bath
4 guests
Average Price:  
$332
19% Cheaper
than normal
AirDNA Score: 69
$167/night

Above the Bike Shop

1 bed
1 bath
4 guests
Average Price:  
$187
11% Cheaper
than normal
AirDNA Score: 69
$245/night

Jewel above the Pub with a view. Walk everywhere!

2 beds
1 bath
4 guests
Average Price:  
$291
16% Cheaper
than normal
AirDNA Score: 69
$195/night

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

1 bed
1 bath
2 guests
Average Price:  
$246
21% Cheaper
than normal
AirDNA Score: 68
$125/night

Rock City Writer''s Studio: bucolic•sauna•walkable!

studio
1 bath
2 guests
Average Price:  
$158
21% 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: 66
$700/night

Secluded home within walking distance to town

4 beds
3.5 baths
8 guests
Average Price:  
$826
15% Cheaper
than normal
AirDNA Score: 64
$275/night

Orange Door Retreat

3 beds
1 bath
6 guests
Average Price:  
$329
16% Cheaper
than normal
AirDNA Score: 64
$145/night

Perfect Woodstock Location- Short Walk to Town

1 bed
1 bath
2 guests
Average Price:  
$176
18% Cheaper
than normal
AirDNA Score: 64
$345/night

Historic 18th-century farmhouse in Woodstock, NY.

4 beds
1.5 baths
8 guests
Average Price:  
$375
8% Cheaper
than normal
AirDNA Score: 64
$140/night

chezbevet-country cabin retreat

1 bed
1 bath
4 guests
Average Price:  
$165
15% Cheaper
than normal
AirDNA Score: 64
$259/night

Beautiful & Spacious Woodstock Home w/ Pool

5 beds
3 baths
10 guests
Average Price:  
$462
44% Cheaper
than normal
AirDNA Score: 63
$285/night

Private & Modern Hot Tub & Fireplace

2 beds
2 baths
6 guests
Average Price:  
$330
14% Cheaper
than normal
AirDNA Score: 62
$260/night

2 BR , Fireplace & Hot Tub @ heart of Woodstock

2 beds
1 bath
6 guests
Average Price:  
$293
11% Cheaper
than normal
AirDNA Score: 61
$299/night

Spacious, Private, Close to Town, Work From Home

3 beds
2.5 baths
7 guests
Average Price:  
$441
32% Cheaper
than normal
AirDNA Score: 59
$275/night

Dove House on Trannery Brook in Woodstock

1 bed
1 bath
2 guests
Average Price:  
$284
3% Cheaper
than normal
AirDNA Score: 59
$200/night

WALK TO TOWN - Hot tub, Stream, Game Room, 4 Br.

4 beds
2.5 baths
9 guests
Average Price:  
$404
50% Cheaper
than normal
AirDNA Score: 58
$350/night

Woodstock Farmhouse Apartment

studio
1 bath
2 guests
Average Price:  
$400
12% Cheaper
than normal
AirDNA Score: 58
$399/night

Sunset Cottage with Mountain Views & Hiking

2 beds
1 bath
4 guests
Average Price:  
$491
19% Cheaper
than normal
AirDNA Score: 56
$395/night

The Cottage in Woodstock

2 beds
1 bath
4 guests
Average Price:  
$516
23% Cheaper
than normal
AirDNA Score: 54
$250/night

Contemporary Cabin With Fireplace

2 beds
1 bath
4 guests
Average Price:  
$274
9% Cheaper
than normal
AirDNA Score: 53
$75/night

Woodstock Studio 1 1/2 miles from town

1 bed
1 bath
2 guests
Average Price:  
$74
1% More
than normal
AirDNA Score: 52
$150/night

Nook above the Pub!

1 bed
1 bath
3 guests
Average Price:  
$212
29% Cheaper
than normal
AirDNA Score: 52
$349/night

Fabulous Village Carriage House w/Garden

2 beds
2 baths
4 guests
Average Price:  
$405
14% Cheaper
than normal
AirDNA Score: 52
$849/night

Idyllic mountain retreat

4 beds
2 baths
6 guests
Average Price:  
$1028
17% Cheaper
than normal
AirDNA Score: 51
$995/night

Luxury Retreat in the Catskills

3 beds
2 baths
6 guests
Average Price:  
$1075
7% Cheaper
than normal
AirDNA Score: 51
$450/night

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

3 beds
2 baths
6 guests
Average Price:  
$574
22% Cheaper
than normal
AirDNA Score: 50
$550/night

Country House in the Hudson Valley near Woodstock

1 bed
1 bath
2 guests
Average Price:  
$175
214% More
than normal
AirDNA Score: 50
$129/night

Woodstock Private Suite: Ensuite Bath/Patio

1 bed
1 bath
2 guests
Average Price:  
$174
26% Cheaper
than normal
AirDNA Score: 50
$170/night

Teahouse Cottage by the River.

studio
1 bath
4 guests
Average Price:  
$261
35% Cheaper
than normal
AirDNA Score: 47
$550/night

Lux Family-Friendly Retreat in Woodstock

3 beds
3 baths
6 guests
Average Price:  
$625
12% Cheaper
than normal
AirDNA Score: 46
$250/night

Woodstock Arts and Crafts Gem

2 beds
2 baths
3 guests
Average Price:  
$299
16% 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:  
$517
23% Cheaper
than normal
AirDNA Score: 41
$400/night

Woodstock Sanctuary Retreat - walk to town!

2 beds
1 bath
4 guests
Average Price:  
$523
24% Cheaper
than normal
AirDNA Score: 41
$140/night

Woodstock Cottage

1 bed
1 bath
3 guests
Average Price:  
$204
31% Cheaper
than normal
AirDNA Score: 30
$199/night

Walk to Town, Onsite Restaurant, Golf Included!

3 beds
1 bath
6 guests
Average Price:  
$255
22% Cheaper
than normal
AirDNA Score: 29
$350/night

Large, welcoming family home, close to town

5 beds
3 baths
10 guests
Average Price:  
$524
33% Cheaper
than normal
AirDNA Score: 28
$1500/night

Stunning contemporary country house

4 beds
3 baths
6 guests
Average Price:  
$1543
3% Cheaper
than normal
AirDNA Score: 25
$222/night

179 Raycliffe Drive, private road

2 beds
2 baths
4 guests
Average Price:  
$269
17% Cheaper
than normal
AirDNA Score: 21
$495/night

Americana time capsule in Woodstock, NY

1 bed
1 bath
2 guests
Average Price:  
$580
15% Cheaper
than normal
AirDNA Score: 14
$290/night

Chic & eclectic retreat at Woodstock/Saugerties!

3 beds
2 baths
6 guests
Average Price:  
$419
31% Cheaper
than normal