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

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73 Best Short-Term Rentals in Chester (Starting from $148)

Millionare Mansion with Grill, Spa, Huge Deck,Views, Game Room, Hiking, More
Millionare Mansion with Grill, Spa, Huge Deck,Views, Game Room, Hiking, More
Apartment
Chester, NY, USA
2.0k from Chester center

Child Friendly, Parking, Kitchen, Breakfast, Balcony/Terrace, Internet, Smoking

4 Bedrooms10 Guests
New to Booking
$894
Average price / night
Check Availability
Spacious 5-bedroom house in serene Chester perfect for families
Spacious 5-bedroom house in serene Chester perfect for families
House
Chester, NY, 10918, United States
1.9k from Chester center

AC, Fitness Equipment, Heater, Internet, No Smoking

5 Bedrooms14 Guests
New to Booking
$727
Average price / night
Check Availability
Elegant Home 7BRs, Game Room, Luxury Yard, Pool
Elegant Home 7BRs, Game Room, Luxury Yard, Pool
Apartment
Chester, NY, USA
3.4k from Chester center

Apartments, Luxury, Accommodations, Pools, Parking, Lodgings, Places to stay, Family

2 Bedrooms16 Guests
New to Booking
$882
Average price / night
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6 bedroom colonial house
6 bedroom colonial house
House
Chester, NY, 10918, United States
2.3k from Chester center

AC, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

5 Bedrooms16 Guests
8.6

Fabulous

4 reviews

$236
Average price / night
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Hudson Valley Retreat with Pool Near Greenwood Lake
Hudson Valley Retreat with Pool Near Greenwood Lake
House
Monroe, NY, USA
5.2k from Chester center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$387
Average price / night
Check Availability
Elegant Home w/7BRs, Game Room, Luxury Yard, Pool
Elegant Home w/7BRs, Game Room, Luxury Yard, Pool
House
Chester, NY, 10918, United States
3.1k from Chester center

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

7 Bedrooms16 Guests
9.0

Fabulous

2 reviews

$845
Average price / night
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Relaxing New York Home with Boat Dock and Lake View!
Relaxing New York Home with Boat Dock and Lake View!
House
Monroe, NY, USA
5.4k from Chester center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms6 Guests
7.5

Good

2 reviews

$289
Average price / night
Check Availability
Summerville Getaway (30 min to Mt. Creek)
Summerville Getaway (30 min to Mt. Creek)
House
Chester, NY, 10918, United States
3.2k from Chester center

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

7 Bedrooms14 Guests
9.8

Exceptional

18 reviews

$982
Average price / night
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Incredible Ranch in the Woods - Peace and Luxury!
Incredible Ranch in the Woods - Peace and Luxury!
House
Chester, New York, USA
5.5k from Chester center

Internet, Pool, Air Conditioner, Parking, Pet Friendly, Child Friendly

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$309
Average price / night
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Charming 1-bedroom Rekindled  Farmhouse Historic Sugar Loaf, NY
Charming 1-bedroom Rekindled Farmhouse Historic Sugar Loaf, NY
Apartment
Chester, NY, 10918, United States
3.5k from Chester center

AC, Heater, Internet, No Smoking

1 Bedroom4 Guests
9.8

Exceptional

8 reviews

$196
Average price / night
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Walton Lake Mountain Lodge
Walton Lake Mountain Lodge
House
Monroe, NY, USA
5.9k from Chester center

Laundry, Wheelchair Accessible, Pool, Hot Tub, Parking, Internet, Child Friendly

4 Bedrooms10 Guests
New to Booking
$498
Average price / night
Check Availability
Spacious Suite (1 hr to Manhattan)
Spacious Suite (1 hr to Manhattan)
House
Chester, NY, 10918, United States
3.6k from Chester center

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

1 Bedroom2 Guests
9.6

Exceptional

8 reviews

$203
Average price / night
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Cozy Beautiful Pondside Luxurious Retreat
Cozy Beautiful Pondside Luxurious Retreat
House
Monroe, NY, USA
6.0k from Chester center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

4 Bedrooms11 Guests
9.5

Superb

2 reviews

$489
Average price / night
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Guesthouse 2 bedroom. 25min-West Point
Guesthouse 2 bedroom. 25min-West Point
House
Chester, NY, 10918, United States
3.6k from Chester center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$183
Average price / night
Check Availability
Craftsman Hideaway at the 1841 Farmhouse
Craftsman Hideaway at the 1841 Farmhouse
Apartment
Chester, NY, USA
6.0k from Chester center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Self-catering

1 Bedroom2 Guests
9.2

Superb

5 reviews

$229
Average price / night
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Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
Apartment
Chester, NY, 10918, United States
4.1k from Chester center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet

2 Bedrooms6 Guests
10.0

Exceptional

55 reviews

$229
Average price / night
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1786 Farm Cottage Honeymoon Suite Renovated 2022
1786 Farm Cottage Honeymoon Suite Renovated 2022
House
Chester, NY, USA
6.0k from Chester center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
9.0

Fabulous

6 reviews

$229
Average price / night
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Spectacular Historic Mansion w/Pool&Tennis
Spectacular Historic Mansion w/Pool&Tennis
House
Goshen, NY, 10924, United States
4.3k from Chester center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Heater, Hot Tub, Internet

10 Bedrooms25 Guests
10.0

Exceptional

18 reviews

$2382
Average price / night
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Very Private Large Home on 22 Acres
Very Private Large Home on 22 Acres
House
Chester, NY, USA
6.2k from Chester center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

5 Bedrooms14 Guests
New to Booking
$913
Average price / night
Check Availability
Country House w/Hot Tub, Deck, Grill & Fire Pit
Country House w/Hot Tub, Deck, Grill & Fire Pit
House
Goshen, NY, 10924, United States
4.3k from Chester center

AC, Balcony, Barbecue, Crib, Dryer, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

61 reviews

$499
Average price / night
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Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
House
Goshen, NY, 10924, United States
4.3k from Chester center

AC, Barbecue, Crib, Dryer, Heater, Internet, Kitchen, Laundry, Living Area

5 Bedrooms10 Guests
10.0

Exceptional

31 reviews

$819
Average price / night
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Spacious 4-bedroom house in awesome Monroe with cool comfort
Spacious 4-bedroom house in awesome Monroe with cool comfort
House
Monroe, NY, 10950, United States
4.4k from Chester center

AC, Fitness Equipment, Heater, Laundry

4 Bedrooms6 Guests
New to Booking
$556
Average price / night
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Spacious Smart Home Retreat on 14 Acres of Nature
Spacious Smart Home Retreat on 14 Acres of Nature
House
Monroe, NY, 10950, United States
4.7k from Chester center

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

5 Bedrooms15 Guests
7.4

Good

3 reviews

$906
Average price / night
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Amazing  Home Near West Point,  Shopping,  Skiing and Legoland
Amazing Home Near West Point, Shopping, Skiing and Legoland
House
Monroe, NY, 10950, United States
5.0k from Chester center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms9 Guests
10.0

Exceptional

14 reviews

$593
Average price / night
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Hudson Valley Retreat w/ Pool Near Greenwood Lake
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Cottage
Monroe, NY, 10950, United States
5.2k from Chester center

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

2 Bedrooms4 Guests
10.0

Exceptional

6 reviews

$271
Average price / night
Check Availability
Lake Views • Spacious 7BR Retreat • Sleeps 12 • Fireplace • King Beds
Lake Views • Spacious 7BR Retreat • Sleeps 12 • Fireplace • King Beds
House
Monroe, NY, 10950, United States
5.2k from Chester center

AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

7 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$1068
Average price / night
Check Availability
Charming  house surrounded lakes and the fresh air of the mountains
Charming house surrounded lakes and the fresh air of the mountains
House
Monroe, NY, 10950, United States
5.4k from Chester center

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

1 Bedroom6 Guests
9.6

Exceptional

19 reviews

$148
Average price / night
Check Availability

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 Chester.

Stay Near Chester's Top Attractions

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Chester Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 73 verified short-term rentals in Chester, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Chester vary depending on location, property size, and travel dates. Rates typically start from around $148 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Chester 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 Chester, 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 Chester often include amenities such as Fireplace/Heating, Child Friendly, and Bedding/Linens, providing a comfortable and convenient stay.

Short-term rentals in Chester 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.