Vacation rentals in Chester

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Top-rated vacation rentals in Chester

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Cottage in Greenwood Lake

4.92 out of 5 average rating, 136 reviews

Cozy home in the Village of Greenwood Lake

Adorable country retreat under an hour from NYC - perfect for a romantic couples getaway or a family of 4. Located in the village, our quaint cottage is walkable to everything; Restaurants, bars, grocer, cvs, bagels, bus stop and even the public beach!! Minutes away from TONS of local attractions; drive-in, skiing, renaissance fair, wineries, shopping, lake activities, orchards, creameries, parks, Appalachian trail, spa, rafting, golf, water park, & so much more. Pets welcome! Permit #21-07603

Sep 2 – 9

€ 137 per night
Guest favorite

Guest suite in Montgomery

4.95 out of 5 average rating, 417 reviews

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 6 people

Nov 10 – 17

€ 129 per night
Guest favorite

Guest suite in Chester

4.96 out of 5 average rating, 224 reviews

Adorable Guest Apartment in Victorian Mansion

This lovely 3rd floor private apartment is in an 1883 Victorian Mansion in Blooming Grove, NY for 1 - 6 people. It is beautifully furnished, and has luxurious beds, so let us know if you need one, two or three bedrooms! The apartment has a private entrance, a claw foot tub, a French door shower, and a kitchenette with sunny breakfast nook. It is freshly renovated and spacious. You will have to take 2 staircases. Our land has a nice view of a field of wildflowers, and our neighbor has cows.

Jan 4 – 11

€ 104 per night

Popular amenities for Chester vacation rentals

Stay near Chester's top sights

The Castle Fun Center78 locals recommend
ShopRite of Chester Plaza, NY13 locals recommend
The Rustic Wheelhouse10 locals recommend
Chester Diner3 locals recommend
Allan's Falafel20 locals recommend
Sugar Loaf Taphouse18 locals recommend

Other great vacation rentals in Chester

Guest favorite

Guesthouse in Suffern

4.91 out of 5 average rating, 110 reviews

Private Studio w/Full Kitchen & Bath

Apr 6 – 13

€ 82 per night
Guest favorite

Guesthouse in Warwick

4.96 out of 5 average rating, 246 reviews

Bellvale Guest House on Solar Powered Mini-estate

Jan 2 – 9

€ 206 per night
Guest favorite

Cabin in Vernon Valley

4.97 out of 5 average rating, 339 reviews

Serenity Cabin, the historic waterfall cabin!

Dec 6 – 13

€ 197 per night
Guest favorite

Cabin in Greenwood Lake

4.92 out of 5 average rating, 171 reviews

Lakeview Cabin at Greenwood Lake

Oct 29 – Nov 5

€ 205 per night
Guest favorite

Cottage in Monroe

5.0 out of 5 average rating, 128 reviews

Cozy Lake Cabin

Aug 5 – 12

€ 510 per night
Guest favorite

Apartment in Warwick

4.9 out of 5 average rating, 522 reviews

The Painted House Warwick, NY

Sep 9 – 16

€ 184 per night
Guest favorite

Apartment in Warwick

4.95 out of 5 average rating, 147 reviews

THE GEM: In The Heart Of It All!

May 22 – 29

€ 235 per night
Guest favorite

Apartment in Warwick

4.98 out of 5 average rating, 346 reviews

Warwick Village Apt w Off St Parking

Sep 3 – 10

€ 191 per night
Guest favorite

Home in Warwick

4.93 out of 5 average rating, 74 reviews

Renovated 2 Bedroom Apartment in Heart of Village

Sep 13 – 20

€ 137 per night
Superhost

Condo in Middletown

5.0 out of 5 average rating, 12 reviews

Chic Haven: Modern & Stylish and Cozy Ambiance

Apr 26 – May 3

€ 103 per night
Superhost

Home in Chester

5.0 out of 5 average rating, 31 reviews

Private Relaxing Secluded Home with heated Pool.

Dec 9 – 16

€ 516 per night
Guest favorite

Home in Chester

5.0 out of 5 average rating, 58 reviews

Millionaire Mansion (Hottub, BBQ, Spa, Games, More

Sep 29 – Oct 6

€ 574 per night

Quick stats about vacation rentals in Chester

Total rentals

10 properties

Local attractions

The Castle Fun Center, ShopRite of Chester Plaza, and NY

Popular amenities

Kitchen, Wifi, and Pool

Wifi availability

10 properties include access to wifi

Total number of reviews

520 reviews

Nightly prices starting at

€ 74 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Orange County
  5. Chester