The Best Airbnb Deals in
Windham, New York

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

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AirDNA Score: 88
$600/night

Serendipity Lake House on Lake Heloise

4 beds
2 baths
16 guests
Average Price:  
$940
36% Cheaper
than normal
AirDNA Score: 86
$225/night

Custom-built Catskills retreat, 7 mins from skiing

2 beds
1 bath
4 guests
Average Price:  
$274
18% Cheaper
than normal
AirDNA Score: 85
$138/night

Hunter / Windham Ski Loft

2 beds
1 bath
5 guests
Average Price:  
$192
28% Cheaper
than normal
AirDNA Score: 81
$200/night

Eagle''s Landing (Windham Mtn. Retreat w/ Hot Tub)

2 beds
2.5 baths
6 guests
Average Price:  
$271
26% Cheaper
than normal
AirDNA Score: 80
$325/night

Charming Home Lg/Mod Kit Hot Tub on Stream FirePit

3 beds
2 baths
6 guests
Average Price:  
$397
18% Cheaper
than normal
AirDNA Score: 79
$215/night

Mountain view apartment, 5mins to Ski Area!

2 beds
2 baths
4 guests
Average Price:  
$173
24% More
than normal
AirDNA Score: 79
$480/night

WELCOMING WINDHAM HOME WITH BREATHTAKING VIEWS

4 beds
2 baths
15 guests
Average Price:  
$650
26% Cheaper
than normal
AirDNA Score: 79
$650/night

Beautiful Windham Ski/Summer House

4 beds
3.5 baths
10 guests
Average Price:  
$691
6% Cheaper
than normal
AirDNA Score: 78
$294/night

Red Fox T.H. & hot tub Springbreak Spring fishing

2 beds
2 baths
4 guests
Average Price:  
$399
26% Cheaper
than normal
AirDNA Score: 78
$1700/night

Windham Home with a Game Room, Hot Tub, Views

5 beds
3 baths
16 guests
Average Price:  
$1835
7% Cheaper
than normal
AirDNA Score: 77
$275/night

Lothbrok - the "B" side - 2 mile slopes & town

3 beds
2 baths
4 guests
Average Price:  
$325
15% Cheaper
than normal
AirDNA Score: 72
$199/night

The Cutest Cabin in Windham 1 min. To ski slope

1 bed
1 bath
2 guests
Average Price:  
$249
20% Cheaper
than normal
AirDNA Score: 71
$999/night

Ski Mountain Chalet w/ Hot Tub, Fireplace, Privacy

6 beds
4 baths
14 guests
Average Price:  
$1192
16% Cheaper
than normal
AirDNA Score: 70
$850/night

Experience winter in the mountains. Pet friendly.

5 beds
3.5 baths
12 guests
Average Price:  
$1000
15% Cheaper
than normal
AirDNA Score: 67
$1067/night

Windham Mountian Chalet with hot tub

5 beds
4 baths
12 guests
Average Price:  
$1045
2% More
than normal
AirDNA Score: 67
$1350/night

Ski Windham — Log home

4 beds
3 baths
10 guests
Average Price:  
$1200
13% More
than normal
AirDNA Score: 66
$368/night

Windham Twnhse-"Make Memories" Free Mtn shuttle

2 beds
2 baths
6 guests
Average Price:  
$373
1% Cheaper
than normal
AirDNA Score: 66
$215/night

The Windham Loft

2 beds
1 bath
5 guests
Average Price:  
$216
0% Cheaper
than normal
AirDNA Score: 65
$383/night

Windham Ski Home!

3 beds
2 baths
8 guests
Average Price:  
$571
33% Cheaper
than normal
AirDNA Score: 65
$300/night

Ski Windham Mountain ( Catskills, NY)

2 beds
2 baths
7 guests
Average Price:  
$375
20% Cheaper
than normal
AirDNA Score: 64
$232/night

Mountainside Ski Deluxe Windham Apt - 1Br 1Bath

1 bed
1 bath
5 guests
Average Price:  
$299
22% Cheaper
than normal
AirDNA Score: 59
$222/night

Small house, Windham, NY

2 beds
1 bath
4 guests
Average Price:  
$247
10% Cheaper
than normal
AirDNA Score: 59
$2453/night

Luxury FAMILY RETREAT with SPA/11 acre/15sleeps

7 beds
4.5 baths
15 guests
Average Price:  
$2678
8% Cheaper
than normal
AirDNA Score: 58
$529/night

Windham Pines Lodge *Hot Tub & Firepit*

3 beds
2 baths
7 guests
Average Price:  
$542
2% Cheaper
than normal
AirDNA Score: 57
$488/night

Villa La Kosta views of GOLF course & Ski Slopes

3 beds
2 baths
6 guests
Average Price:  
$524
7% Cheaper
than normal
AirDNA Score: 57
$375/night

The Windham Cabin w/ Hot Tub

3 beds
2 baths
6 guests
Average Price:  
$429
13% Cheaper
than normal
AirDNA Score: 57
$135/night

Windham Condo

2 beds
2 baths
5 guests
Average Price:  
$183
26% Cheaper
than normal
AirDNA Score: 56
$1549/night

Luxury Log Home with Ski Windham Views

5 beds
4.5 baths
16 guests
Average Price:  
$1948
20% Cheaper
than normal
AirDNA Score: 56
$250/night

Windham Ski house, beautiful views

3 beds
1.5 baths
4 guests
Average Price:  
$276
9% Cheaper
than normal
AirDNA Score: 55
$287/night

ski/summer house close to windham & hunter mtn.

3 beds
3 baths
9 guests
Average Price:  
$296
3% Cheaper
than normal
AirDNA Score: 54
$275/night

Windham ''Rondelet'' House - Close to Town & Mtn!

2 beds
2 baths
5 guests
Average Price:  
$263
5% More
than normal
AirDNA Score: 54
$2777/night

Ideal Catskills Retreat 5 Min to Windham Mountain!

8 beds
6.5 baths
16 guests
Average Price:  
$2748
1% More
than normal
AirDNA Score: 54
$203/night

Windham Ski & Summer Retreat - Near Everything!

2 beds
2.5 baths
5 guests
Average Price:  
$330
38% Cheaper
than normal
AirDNA Score: 53
$198/night

Windham Mountain Retreat.

3 beds
2 baths
9 guests
Average Price:  
$353
44% Cheaper
than normal
AirDNA Score: 53
$125/night

Studio 3 BEDS-SLEEP 4

studio
1 bath
3 guests
Average Price:  
$144
13% Cheaper
than normal
AirDNA Score: 51
$399/night

Private family home! 4 miles to Windham Mtn!

3 beds
3 baths
10 guests
Average Price:  
$650
39% Cheaper
than normal
AirDNA Score: 51
$675/night

Windham 5 min to slopes, sleeps 15, hot tub

4 beds
3.5 baths
15 guests
Average Price:  
$715
6% Cheaper
than normal
AirDNA Score: 51
$391/night

Perfect Family Cabin on 5 acres - 5 min to Windham

4 beds
2.5 baths
10 guests
Average Price:  
$569
31% Cheaper
than normal
AirDNA Score: 51
$454/night

Windham Townhouse. Base of Mountain

3 beds
3 baths
10 guests
Average Price:  
$586
23% Cheaper
than normal
AirDNA Score: 50
$1217/night

Luxury Home on Windham Mountain

4 beds
4 baths
11 guests
Average Price:  
$1262
4% Cheaper
than normal
AirDNA Score: 50
$500/night

The Corral''s in Windham

3 beds
2 baths
11 guests
Average Price:  
$542
8% Cheaper
than normal
AirDNA Score: 50
$288/night

The Mountain House with large private pond

5 beds
2 baths
10 guests
Average Price:  
$519
45% Cheaper
than normal
AirDNA Score: 47
$367/night

Windham Mountain NY Catskills

3 beds
2 baths
6 guests
Average Price:  
$381
4% Cheaper
than normal
AirDNA Score: 44
$539/night

Near Hunter and Windham, Crystal Pond, 4 BR 3.5 BA

4 beds
3.5 baths
8 guests
Average Price:  
$730
26% Cheaper
than normal
AirDNA Score: 41
$300/night

Waterfront secluded log-house w/sauna, games, more

3 beds
2 baths
10 guests
Average Price:  
$459
35% Cheaper
than normal
AirDNA Score: 37
$999/night

ON MOUNTAIN - 4 BED, 4 BATH RETREAT

4 beds
3.5 baths
14 guests
Average Price:  
$840
19% More
than normal
AirDNA Score: 29
$267/night

2 BR 1.5 BH in ranch on 5 ac strong Wi-Fi 360 view

2 beds
1.5 baths
8 guests
Average Price:  
$331
19% Cheaper
than normal
AirDNA Score: 29
$550/night

Perfect Family Getaway- 3BD, 3BATH Pool Hot Tub

3 beds
3 baths
12 guests
Average Price:  
$583
6% Cheaper
than normal
AirDNA Score: 29
$202/night

Streamside Cabin

3 beds
1 bath
6 guests
Average Price:  
$271
25% Cheaper
than normal
AirDNA Score: 29
$430/night

Windham Streamside Country House - 5 min to mtn

6 beds
3 baths
10 guests
Average Price:  
$519
17% Cheaper
than normal
AirDNA Score: 26
$175/night

Cozy cute and brite

1 bed
1 bath
2 guests
Average Price:  
$275
36% Cheaper
than normal
AirDNA Score: 26
$279/night

Unique Windham Townhouse/Loft-Like Openness/ Slp 6

2 beds
2 baths
6 guests
Average Price:  
$230
21% More
than normal
AirDNA Score: 21
$180/night

Mitchell Hollow Home

2 beds
1 bath
4 guests
Average Price:  
$214
16% Cheaper
than normal
AirDNA Score: 13
$500/night

The Xenia - A 4 Seasons Home

4 beds
3 baths
14 guests
Average Price:  
$583
14% Cheaper
than normal
AirDNA Score: 0
$759/night

Luxurious, 4500 sq foot home in center of Windham

4 beds
3 baths
10 guests
Average Price:  
$960
21% Cheaper
than normal