Short-Term Rentals in Chatham, NY: Compare 10+ Sites & Save

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57 Best Short-Term Rentals in Chatham (Starting from $125)

Secluded w Deck Views Hot Tub Ping Pong Hudson in the Berks by AvantStay
Secluded w Deck Views Hot Tub Ping Pong Hudson in the Berks by AvantStay
House
East Chatham, NY, USA
7.4k from Chatham center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Hot tubs, Places to stay

1 Bedroom10 Guests
New to Booking
$678
Average price / night
Check Availability
Renovated house. Built in 1890s. No neighbors in sight.
Renovated house. Built in 1890s. No neighbors in sight.
House
Chatham, NY, 12037, United States
0.4k from Chatham center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
9.0

Fabulous

2 reviews

$309
Average price / night
Check Availability
Private Hot Tub Hudson Valley Cabin Retreat!
Private Hot Tub Hudson Valley Cabin Retreat!
House
NY, USA
8.3k from Chatham center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Hot tubs, Places to stay

3 Bedrooms12 Guests
New to Booking
$868
Average price / night
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Gorgeous large renovated historic home on 10 acres with pool
Gorgeous large renovated historic home on 10 acres with pool
House
Chatham, NY, 12037, United States
2.2k from Chatham center

AC, Arcade, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet

5 Bedrooms14 Guests
10.0

Exceptional

25 reviews

$1041
Average price / night
Check Availability
Secluded Estate w Guest House Private Pond Gym Movie Theater Sunny Pond
Secluded Estate w Guest House Private Pond Gym Movie Theater Sunny Pond
House
NY, USA
8.7k from Chatham center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom20 Guests
New to Booking
$2706
Average price / night
Check Availability
2,000 sq ft loft located \"downtown\" with access to dining..shops...movie theater
2,000 sq ft loft located \"downtown\" with access to dining..shops...movie theater
Apartment
Chatham, NY, 12037, United States
2.9k from Chatham center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

14 reviews

$426
Average price / night
Check Availability
Secluded Berkshires Estate Private PondPoolTheater Gym Sunny Pond
Secluded Berkshires Estate Private PondPoolTheater Gym Sunny Pond
House
NY, USA
8.7k from Chatham center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom16 Guests
New to Booking
$2194
Average price / night
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Sugar Shack - 300 square feet of pure sweetness.
Sugar Shack - 300 square feet of pure sweetness.
House
Chatham, NY, 12037, United States
3.1k from Chatham center

AC, Balcony, Barbecue, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

1 Bedroom2 Guests
10.0

Exceptional

3 reviews

$368
Average price / night
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3 Bedroom Hudson Valley Loft with private porch in the heart of Chatham Village
3 Bedroom Hudson Valley Loft with private porch in the heart of Chatham Village
Apartment
Chatham, NY, 12037, United States
3.2k from Chatham center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms5 Guests
New to Booking
$361
Average price / night
Check Availability
Spacious rustic house in Chatham, NY
Spacious rustic house in Chatham, NY
House
Chatham, NY, 12037, United States
3.4k from Chatham center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

4 Bedrooms10 Guests
New to Booking
$329
Average price / night
Check Availability
BLUSH: Boutique TINY home*private spa*walk to town
BLUSH: Boutique TINY home*private spa*walk to town
House
Chatham, NY, 12037, United States
3.5k from Chatham center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

1 Bedroom2 Guests
10.0

Exceptional

7 reviews

$330
Average price / night
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Hudson Valley  Berkshires Cottage - Great View, Private & Quiet
Hudson Valley Berkshires Cottage - Great View, Private & Quiet
Cottage
Austerlitz, NY, 12165, United States
3.6k from Chatham center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
New to Booking
$199
Average price / night
Check Availability
La Petite Maison, Chatham, NY
La Petite Maison, Chatham, NY
House
Chatham, NY, 12037, United States
4.0k from Chatham center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$228
Average price / night
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Cozy Chatham Retreat
Cozy Chatham Retreat
House
Chatham, NY, 12037, United States
4.0k from Chatham center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
9.8

Exceptional

10 reviews

$243
Average price / night
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Modern Log Chalet - 10 acres, views, and a pond!
Modern Log Chalet - 10 acres, views, and a pond!
House
Chatham, NY, 12037, United States
4.1k from Chatham center

AC, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry, No Smoking, Toys

3 Bedrooms12 Guests
10.0

Exceptional

8 reviews

$645
Average price / night
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Chatham Cozy Country Retreat
Chatham Cozy Country Retreat
House
Chatham, NY, 12037, United States
4.3k from Chatham center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

4 reviews

$188
Average price / night
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Nordic Cabin: Light-Filled + Spacious w/Firepit
Nordic Cabin: Light-Filled + Spacious w/Firepit
House
Chatham, NY, 12037, United States
4.8k from Chatham center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

3 Bedrooms8 Guests
New to Booking
$331
Average price / night
Check Availability
Red Rock Summit: Pool | Privacy + Views | Sauna
Red Rock Summit: Pool | Privacy + Views | Sauna
House
East Chatham, NY, 12060, United States
5.4k from Chatham center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
6.0

Review score

1 reviews

$1090
Average price / night
Check Availability
Birds’ Nest Bungalow
Birds’ Nest Bungalow
House
East Chatham, NY, 12060, United States
5.5k from Chatham center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms4 Guests
10.0

Exceptional

21 reviews

$417
Average price / night
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Charming Cabin in the Woods. POOL!
Charming Cabin in the Woods. POOL!
Cabin
Ghent, NY, 12075, United States
5.6k from Chatham center

Barbecue, Fireplace, Free Parking, Hot Tub, Internet, Kitchen, Microwave, No Smoking, Patio

1 Bedroom3 Guests
9.8

Exceptional

6 reviews

$125
Average price / night
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8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
House
Old Chatham, NY, 12136, United States
5.6k from Chatham center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, No Smoking

4 Bedrooms8 Guests
New to Booking
$418
Average price / night
Check Availability
Spacious Garage Loft with AC and View!
Spacious Garage Loft with AC and View!
Apartment
Ghent, NY, 12075, United States
5.7k from Chatham center

AC, Free Parking, Heater, Hot Tub, Internet, Microwave, No Smoking, Pool

1 Bedroom3 Guests
New to Booking
$132
Average price / night
Check Availability
Beebehill house\n\n
Beebehill house\n\n
House
Chatham, NY, 12037, United States
5.9k from Chatham center

AC, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms8 Guests
New to Booking
$536
Average price / night
Check Availability
Suite 3 - Quiet and private accommodations in a country setting.
Suite 3 - Quiet and private accommodations in a country setting.
House
Spencertown, NY, 12165, United States
6.0k from Chatham center

AC, Extra Bed, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$263
Average price / night
Check Availability
Mountain View Retreat in Hudson Valley near Berkshire Attractions
Mountain View Retreat in Hudson Valley near Berkshire Attractions
Cottage
Old Chatham, NY, 12136, United States
6.1k from Chatham center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms6 Guests
10.0

Exceptional

10 reviews

$273
Average price / night
Check Availability
Suite 4 - Quiet and private accommodations in a country setting.
Suite 4 - Quiet and private accommodations in a country setting.
Apartment
Spencertown, NY, 12165, United States
6.1k from Chatham center

AC, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms2 Guests
10.0

Exceptional

3 reviews

$266
Average price / night
Check Availability
Suite 5 - Quiet and private accommodations in a country setting.
Suite 5 - Quiet and private accommodations in a country setting.
Apartment
Spencertown, NY, 12165, United States
6.1k from Chatham center

AC, Extra Bed, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Patio

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$266
Average price / night
Check Availability

Other accommodation types in Chatham:

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Chatham.

Chatham Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 57 verified short-term rentals in Chatham, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Chatham vary depending on location, property size, and travel dates. Rates typically start from around $125 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Chatham include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Chatham, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Chatham often include amenities such as Fireplace/Heating, Wellness Facilities, and Bedding/Linens, providing a comfortable and convenient stay.

Short-term rentals in Chatham are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.