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Vacation rentals in Chatham, New York, United States

Serene Farmhouse Villa | Pool | Hot Tub | Grill

Serene Farmhouse Villa | Pool | Hot Tub | Grill

Serene Farmhouse Villa | Pool | Hot Tub | Grill

Serene Farmhouse Villa | Pool | Hot Tub | Grill

Serene Farmhouse Villa | Pool | Hot Tub | Grill

Serene Farmhouse Villa | Pool | Hot Tub | Grill

3 bedrooms·2 baths

Chatham • New York

2.654,50 $ USD gesamt für 3 Nächte

30. Mai – 2. Juni 2027

Serene Farmhouse Villa | Pool | Hot Tub | Grill

Serene Farmhouse Villa | Pool | Hot Tub | Grill

Serene Farmhouse Villa | Pool | Hot Tub | Grill

Serene Farmhouse Villa | Pool | Hot Tub | Grill

Serene Farmhouse Villa | Pool | Hot Tub | Grill

Serene Farmhouse Villa | Pool | Hot Tub | Grill

3 bedrooms·2 baths

Chatham • New York

2.654,50 $ USD gesamt für 3 Nächte

30. Mai – 2. Juni 2027

Welcome to Austerlitz!

Open living space with fireplace.

Private cottage close to shopping, dining, skiing. image 4

Kitchen with all the essentials

Cozy love seat and fireplace.

Private cottage close to shopping, dining, skiing.

3 bedrooms·2 baths

Austerlitz • New York

5(6 reviews)

960,00 $ USD gesamt für 3 Nächte

17.–20. Nov. 2026

Hilltop House and its barn in the snow!

Hilltop House

4 bedrooms·4 baths

Canaan • New York

8.350,00 $ USD gesamt für 30 Nächte

17. Nov. – 17. Dez. 2026

Garden-level Country Oasis Apt.

Garden-level Country Oasis Apt.

Garden-level Country Oasis Apt.

Garden-level Country Oasis Apt.

Garden-level Country Oasis Apt.

Garden-level Country Oasis Apt.

2 bedrooms·1 bath

Nassau • New York

5(3 reviews)

2.164,00 $ USD gesamt für 28 Nächte

17. Nov. – 15. Dez. 2026

Hudson Haven image 2

Hudson Haven

3 bedrooms·2 baths

Hudson • New York

4.82(104 reviews)

935,00 $ USD gesamt für 3 Nächte

20.–23. Nov. 2026

Into the Woods- Berkshire Cabin Retreat! image 1

Into the Woods- Berkshire Cabin Retreat! image 2

Into the Woods- Berkshire Cabin Retreat! image 3

Into the Woods- Berkshire Cabin Retreat! image 4

Into the Woods- Berkshire Cabin Retreat! image 5

Into the Woods- Berkshire Cabin Retreat!

3 bedrooms·2 baths

East Nassau • New York

5(60 reviews)

1.078,00 $ USD gesamt für 3 Nächte

17.–20. Nov. 2026

Cemetery Schoolhouse l image 1

Cemetery Schoolhouse l image 2

Cemetery Schoolhouse l image 3

Cemetery Schoolhouse l image 4

Cemetery Schoolhouse l image 5

Cemetery Schoolhouse l

1 bedroom·1 bath

Hudson • New York

4.88(238 reviews)

2.250,00 $ USD gesamt für 30 Nächte

7. Dez. 2026 – 6. Jan. 2027

Asian Cemetery Schoolhouse image 1

Chinese Wedding- Opium Bed!!!!!

a really long table for all your imaginary friends

Painting by Marie Stella. Dresser to stash all the goodies you get on Warren

this looks really nice doesnt it? thanks.

Asian Cemetery Schoolhouse

1 bedroom·1 bath

Hudson • New York

2.170,00 $ USD gesamt für 30 Nächte

17. Nov. – 17. Dez. 2026

Gorgeous Views - House on Copake Lake

Gorgeous Views - House on Copake Lake

Typical Bedroom

Gorgeous Views - House on Copake Lake

3 bedrooms·1½ baths

Hillsdale • New York

3.085,00 $ USD gesamt für 30 Nächte

17. Nov. – 17. Dez. 2026

Private country estate w/ pool and tennis court image 5

Private country estate w/ pool and tennis court image 2

Private country estate w/ pool and tennis court image 1

Private country estate w/ pool and tennis court image 3

Private country estate w/ pool and tennis court image 7

Private country estate w/ pool and tennis court

4 bedrooms·3 baths

Ancram • New York

4.88(34 reviews)

1.400,00 $ USD gesamt für 3 Nächte

17.–20. Nov. 2026

Peaceful Cabin on 2.5 wooded acres- 3 Bed/2.5 bath

Peaceful Cabin on 2.5 wooded acres- 3 Bed/2.5 bath

Peaceful Cabin on 2.5 wooded acres- 3 Bed/2.5 bath

Peaceful Cabin on 2.5 wooded acres- 3 Bed/2.5 bath

Peaceful Cabin on 2.5 wooded acres- 3 Bed/2.5 bath

Peaceful Cabin on 2.5 wooded acres- 3 Bed/2.5 bath

3 bedrooms·2 baths

Catskill • New York

5(14 reviews)

1.400,00 $ USD gesamt für 3 Nächte

17.–20. Nov. 2026

Living Room | Comfortable couch and queen size pull-out bed (must request linens for pull-out bed BEFORE your stay), and a Smart TV to log into your personal streaming accounts. Suitable for couples getaways, friends trips and solo travelers.

Smart Roku TV | Log into your own streaming accounts: Netflix, Hulu, Disney+ etc.

Catch up on your favorite tv shows, watch movies or Roku’s free live tv options.

1BR Garden Apt.| W/D + Fire Pit for Summer Nights! image 3

1BR Garden Apt.| W/D + Fire Pit for Summer Nights! image 4

Full Kitchen | Equipped with full size stove and oven, microwave, toaster, cutlery, pots and pans, dining table with 3 stools. Cook your favorite meals or heat up your leftovers from the many tasty restaurants in walking distance.

1BR Garden Apt.| W/D + Fire Pit for Summer Nights!

1 bedroom·1 bath

Albany • New York

4.94(34 reviews)

451,13 $ USD gesamt für 3 Nächte

17.–20. Nov. 2026

Peaceful backyard with fire pit, Adirondack chairs, and stunning fall foliage

Cozy backyard fire pit with Adirondack chairs for relaxing evenings

Peaceful Catskills Getaway - Cozy Studio Loft

Charming private entry with garden views, open yard, and peaceful outdoor setting

Peaceful pasture views with grazing horses and classic country charm

Peaceful Catskills Getaway - Cozy Studio Loft

0 bedrooms·1 bath

Greene County • New York

610,50 $ USD gesamt für 3 Nächte

17.–20. Nov. 2026

Nature Escape: Fire Pit • Games • Near Windham Mtn

Nature Escape: Fire Pit • Games • Near Windham Mtn

Nature Escape: Fire Pit • Games • Near Windham Mtn

Nature Escape: Fire Pit • Games • Near Windham Mtn

Nature Escape: Fire Pit • Games • Near Windham Mtn

Nature Escape: Fire Pit • Games • Near Windham Mtn

3 bedrooms·3 baths

Greene County • New York

1.001,71 $ USD gesamt für 3 Nächte

1.–4. Juni 2027

Dining Room Table

Ironworks Urban Retreat

2 bedrooms·1 bath

Troy • New York

5(3 reviews)

597,05 $ USD 561,77 $ USD gesamt für 3 Nächte

18.–21. Nov. 2026

The Collar City Oasis

2 bedrooms·1 bath

Troy • New York

5(3 reviews)

507,93 $ USD 481,57 $ USD gesamt für 3 Nächte

17.–20. Nov. 2026

Uncle Sam's Hideaway

3 bedrooms·1 bath

Troy • New York

5(2 reviews)

624,18 $ USD 586,19 $ USD gesamt für 3 Nächte

17.–20. Nov. 2026

Our lil slice of paradise

Idyllic Esopus River Retreat

4 bedrooms·3 baths

Saugerties • New York

3.325,00 $ USD gesamt für 3 Nächte

17.–20. Nov. 2026

Large Family/Group | Lake House | Hot Tub | Sauna | Kayak | Fire Pit | Beach | Arcade

Large Family/Group | Lake House | Hot Tub | Sauna | Kayak | Fire Pit | Beach | Arcade

Large Family/Group | Lake House | Hot Tub | Sauna | Kayak | Fire Pit | Beach | Arcade

Large Family/Group | Lake House | Hot Tub | Sauna | Kayak | Fire Pit | Beach | Arcade

Large Family/Group | Lake House | Hot Tub | Sauna | Kayak | Fire Pit | Beach | Arcade

Large Family/Group | Lake House | Hot Tub | Sauna | Kayak | Fire Pit | Beach | Arcade

5 bedrooms·2 baths

Saugerties • New York

5(28 reviews)

3.023,75 $ USD gesamt für 3 Nächte

17.–20. Nov. 2026

Esopus Waterfront | Arcade | Sauna | Kayak | Hot Tub

Esopus Waterfront | Arcade | Sauna | Kayak | Hot Tub

Esopus Waterfront | Arcade | Sauna | Kayak | Hot Tub

Esopus Waterfront | Arcade | Sauna | Kayak | Hot Tub

Esopus Waterfront | Arcade | Sauna | Kayak | Hot Tub

Esopus Waterfront | Arcade | Sauna | Kayak | Hot Tub

2 bedrooms·1 bath

Saugerties • New York

5(6 reviews)

2.060,80 $ USD gesamt für 3 Nächte

22.–25. Nov. 2026

Saugerties Waterfront | Fishing | Kayak | Fire Pit | Sauna | Hot Tub | Beach

Saugerties Waterfront | Fishing | Kayak | Fire Pit | Sauna | Hot Tub | Beach

Saugerties Waterfront | Fishing | Kayak | Fire Pit | Sauna | Hot Tub | Beach

Saugerties Waterfront | Fishing | Kayak | Fire Pit | Sauna | Hot Tub | Beach

Saugerties Waterfront | Fishing | Kayak | Fire Pit | Sauna | Hot Tub | Beach

Saugerties Waterfront | Fishing | Kayak | Fire Pit | Sauna | Hot Tub | Beach

3 bedrooms·1 bath

Saugerties • New York

5(6 reviews)

2.164,45 $ USD gesamt für 3 Nächte

22.–25. Nov. 2026