Title: Chester Vacation Home Rentals from CA $213: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d6046665.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d6046665.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d6046665.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d6046665.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester vacation homes ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/424d87c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/9832ea44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/e5f1d678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/92f8429f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Highland Falls [](https://www.expedia.ca/Highland-Falls-Hotels-House-On-The-Babbling-Brook-Quiet-2BR-King-Bed.h113522235.Hotel-Information) 10/10 Exceptional (6 reviews) "Good stay, awesome place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott G. CA $126 CA $477 total includes taxes & fees Jan 16 - Jan 17 [](https://www.expedia.ca/Highland-Falls-Hotels-House-On-The-Babbling-Brook-Quiet-2BR-King-Bed.h113522235.Hotel-Information) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/7ad8e5a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/b762fce3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/82ecc5c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/cf889632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Highland Falls [](https://www.expedia.ca/Highland-Falls-Hotels-Sleek-Escape-Modern-3-BR-4-Min-From-West-Point.h110986250.Hotel-Information) 10/10 Exceptional (3 reviews) "The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julio J. CA $129 CA $559 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Highland-Falls-Hotels-Sleek-Escape-Modern-3-BR-4-Min-From-West-Point.h110986250.Hotel-Information) ![Apartment](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706320/ce02298f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706320/c81a0e54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706320/2107cf79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706320/24d963c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Monroe [](https://www.expedia.ca/Monroe-Hotels-Rustic-Lakefront-Studio-With-Deck-Workspace.h123706320.Hotel-Information) CA $128 CA $322 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Monroe-Hotels-Rustic-Lakefront-Studio-With-Deck-Workspace.h123706320.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/117000000/116300000/116293600/116293556/e4cec53f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/117000000/116300000/116293600/116293556/80ec6f48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/117000000/116300000/116293600/116293556/4cc093aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116300000/116293600/116293556/d8b7ae3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Warwick [](https://www.expedia.ca/Warwick-Hotels-Room-1-At-The-Warwick-Inn-Cozy-Elegance-In-The-Heart-Of-Town.h116293556.Hotel-Information) 9.4/10 Exceptional (8 reviews) "I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin R. CA $121 CA $213 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Warwick-Hotels-Room-1-At-The-Warwick-Inn-Cozy-Elegance-In-The-Heart-Of-Town.h116293556.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/6a09d677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/719e347a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/f77cbaf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/3207c5e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Highland Falls [](https://www.expedia.ca/Highland-Falls-Hotels-Lovely-3BR-Home-With-Parking-Walk-To-WP-Gate.h105177891.Hotel-Information) 10/10 Exceptional (7 reviews) "Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Briana T. CA $211 CA $427 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Highland-Falls-Hotels-Lovely-3BR-Home-With-Parking-Walk-To-WP-Gate.h105177891.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/6b825ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/973f29b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/6f93013a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/8fad8a9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Highland Falls [](https://www.expedia.ca/Highland-Falls-Hotels-3BR-West-Point-Retreat-3min-To-Back-Gate-King-Bed.h113522229.Hotel-Information) 7.6/10 Good (5 reviews) "Wonderful stay! The property is within walking distance of the little downtown area & had driveway parking. It was clean & plenty spacious. Property owners had great communication! This is a property with 2 units, but we were not bothered by any extra noise. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Waylon J. CA $153 CA $608 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Highland-Falls-Hotels-3BR-West-Point-Retreat-3min-To-Back-Gate-King-Bed.h113522229.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/be15b260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/0c2d8c1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/8cbcd139.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/116022ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Highland Falls [](https://www.expedia.ca/Highland-Falls-Hotels-Fabulous-3bdrm-Home-Wparking.h114378708.Hotel-Information) 9.0/10 Wonderful (4 reviews) "Clean home, conveniently located to West Point. Very comfortable beds. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danielle B. CA $211 CA $416 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Highland-Falls-Hotels-Fabulous-3bdrm-Home-Wparking.h114378708.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/ef9b23f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/02671128.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/c86208ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/d5087de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Fishkill [](https://www.expedia.ca/Fishkill-Hotels-Large-Relaxing-Family-Retreat-In-The-Hudson-Valley-With-Theatre-And-Gazebo.h111183358.Hotel-Information) 9.4/10 Exceptional (54 reviews) "Quiet, clean and comfortable! Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph G. CA $344 CA $442 total includes taxes & fees Jan 16 - Jan 17 [](https://www.expedia.ca/Fishkill-Hotels-Large-Relaxing-Family-Retreat-In-The-Hudson-Valley-With-Theatre-And-Gazebo.h111183358.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/78000000/77290000/77280600/77280503/541d91ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77290000/77280600/77280503/d2d9d4e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/78000000/77290000/77280600/77280503/537494b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/78000000/77290000/77280600/77280503/5a612bda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Goshen [](https://www.expedia.ca/Goshen-Hotels-Renovated-House-WHot-Tub.h77280503.Hotel-Information) 10/10 Exceptional (59 reviews) "Clean and comfortable accommodations, very close to Legoland and Castle Fun Center! The kids loved the room with bunk beds, and it had a big selection of children's books and some toys, which was a nice bonus!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer K. CA $344 CA $662 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Goshen-Hotels-Renovated-House-WHot-Tub.h77280503.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122930000/122929100/122929001/120febc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122930000/122929100/122929001/2f9d1a89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/123000000/122930000/122929100/122929001/bb90272b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/123000000/122930000/122929100/122929001/e249d080.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Cornwall [](https://www.expedia.ca/Cornwall-Hotels-Storm-King-At-Narnia-Welcome-To-A-Slice-Of-Paradise-In-The-Hudson-Valley.h122929001.Hotel-Information) 10/10 Exceptional (2 reviews) "We really enjoyed our short stay at the house - it was extremely clean, the beds were comfortable, and the whole house was warm and cozy. There were thoughtful little touches all around the house - from fluffy socks for us to extra blankets, motion-sensor nightlights, and a fully equipped kitchen. Everything is newly renovated and updated. Views of the surrounding mountains are beautiful and the location is quiet and peaceful. We would visit again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne R. CA $300 CA $586 total includes taxes & fees Jan 16 - Jan 17 [](https://www.expedia.ca/Cornwall-Hotels-Storm-King-At-Narnia-Welcome-To-A-Slice-Of-Paradise-In-The-Hudson-Valley.h122929001.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/32d0bc6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/e5a3641b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/449fc3a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/d9fd7f11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lake Peekskill [](https://www.expedia.ca/Lake-Peekskill-Hotels-Contemporary-Cozy-Cottage.h102145832.Hotel-Information) 10/10 Exceptional (31 reviews) "Very clean comfortable quiet place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mauro C. CA $312 CA $580 total includes taxes & fees Jan 16 - Jan 17 [](https://www.expedia.ca/Lake-Peekskill-Hotels-Contemporary-Cozy-Cottage.h102145832.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/122000000/121520000/121517700/121517645/ac8a10de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121520000/121517700/121517645/139bc94d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Towels, soap, toilet paper](https://images.trvl-media.com/lodging/122000000/121520000/121517700/121517645/e9c28575.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/122000000/121520000/121517700/121517645/75a976f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Middletown [](https://www.expedia.ca/Middletown-Hotels-Charming-Bungalow-In-Lovely-Middletown-NY.h121517645.Hotel-Information) CA $187 CA $272 total includes taxes & fees Jan 16 - Jan 17 [](https://www.expedia.ca/Middletown-Hotels-Charming-Bungalow-In-Lovely-Middletown-NY.h121517645.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/83000000/82880000/82871400/82871343/26e596cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/83000000/82880000/82871400/82871343/0f6294ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/83000000/82880000/82871400/82871343/880c573c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/83000000/82880000/82871400/82871343/6002474e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Vernon Township [](https://www.expedia.ca/Vernon-Hotels-Mountain-Creek-Lovely-1-BedroomPoolJacuzziKing-BedSki-InOut.h82871343.Hotel-Information) 9.4/10 Exceptional (46 reviews) "Great place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michele B. CA $199 CA $422 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Vernon-Hotels-Mountain-Creek-Lovely-1-BedroomPoolJacuzziKing-BedSki-InOut.h82871343.Hotel-Information) ![House](https://images.trvl-media.com/lodging/122000000/121910000/121901300/121901234/af5902b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/122000000/121910000/121901300/121901234/d25435a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/122000000/121910000/121901300/121901234/a935500d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/122000000/121910000/121901300/121901234/e36fc455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Cornwall [](https://www.expedia.ca/Cornwall-Hotels-West-Point-Villa-Jacuzzi-Pool-BBQ-Games-Pets.h121901234.Hotel-Information) CA $425 CA $1,267 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Cornwall-Hotels-West-Point-Villa-Jacuzzi-Pool-BBQ-Games-Pets.h121901234.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/102000000/101640000/101630700/101630631/8b09ea65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101640000/101630700/101630631/6caa4a76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/102000000/101640000/101630700/101630631/9983c1a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101640000/101630700/101630631/f0ea9feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Vernon Township [](https://www.expedia.ca/Vernon-Hotels-Private-Mountain-Creek-Getaway.h101630631.Hotel-Information) 8.8/10 Excellent (6 reviews) "The property is very comfortable and clean. It is convenient to the ski area, Warwick, New York's apple orchards and fun main street shopping, Penning's Cidery & Orchard. The driveway is steep, if you have multiple cars, parking across the street (if allowed) may be preferred." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia S. CA $256 CA $599 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Vernon-Hotels-Private-Mountain-Creek-Getaway.h101630631.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122970000/122963500/122963409/a7f39d48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/123000000/122970000/122963500/122963409/85a87f1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122970000/122963500/122963409/64348083.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122970000/122963500/122963409/09af6873.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Monroe [](https://www.expedia.ca/Monroe-Hotels-Lakeview-Escape-Scenic-Deck-Wi-Fi-Fire-Pit.h122963409.Hotel-Information) 7.0/10 Good (2 reviews) "Overall the house is lovely. It's evident that the owners are taking great care to make the house welcoming and a good environment for guests. The views are remarkable. Must love stairs." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tallie C. CA $196 CA $606 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Monroe-Hotels-Lakeview-Escape-Scenic-Deck-Wi-Fi-Fire-Pit.h122963409.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/101000000/100670000/100661800/100661800/eb403423.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/101000000/100670000/100661800/100661800/2c7bb45a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100670000/100661800/100661800/d7a17c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100670000/100661800/100661800/2c6360ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Greenwood Lake [](https://www.expedia.ca/Greenwood-Lake-Hotels-Waterfront-Modern-Home-WFast-Wifi-400m-From-DT.h100661800.Hotel-Information) 9.8/10 Exceptional (32 reviews) "Beautiful property, the photos do it justice, but the location (and peace) of the property can't be seen in just pictures. The family agreed one of the best places we've gotten, wonderful way to spend a late summer week on the lake." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Devan S. CA $278 CA $707 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Greenwood-Lake-Hotels-Waterfront-Modern-Home-WFast-Wifi-400m-From-DT.h100661800.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/64000000/63530000/63528000/63527962/7aab0afd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/64000000/63530000/63528000/63527962/34ea7109.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/64000000/63530000/63528000/63527962/b732456b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![](https://images.trvl-media.com/lodging/64000000/63530000/63528000/63527962/a0f6a3e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Newburgh [](https://www.expedia.ca/Newburgh-Hotels-Large.h63527962.Hotel-Information) 9.0/10 Wonderful (15 reviews) "Very cozy stay with responsive host" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Adhith P. CA $500 CA $671 total includes taxes & fees Jan 16 - Jan 17 [](https://www.expedia.ca/Newburgh-Hotels-Large.h63527962.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106650000/106647200/106647189/5b4bebd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106650000/106647200/106647189/bc63286a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106650000/106647200/106647189/e6f59d49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106650000/106647200/106647189/885ee2d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Goshen [](https://www.expedia.ca/Goshen-Hotels-Luxury-3-Bedroom-Fully-Renovated-House-In-Goshen-With-Brand-New-Furniture.h106647189.Hotel-Information) 9.0/10 Wonderful (12 reviews) "Great location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alozie E. CA $400 CA $608 total includes taxes & fees Jan 16 - Jan 17 [](https://www.expedia.ca/Goshen-Hotels-Luxury-3-Bedroom-Fully-Renovated-House-In-Goshen-With-Brand-New-Furniture.h106647189.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/70000000/69550000/69540600/69540509/5a25293d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69550000/69540600/69540509/7f413749.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/70000000/69550000/69540600/69540509/1c631163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69550000/69540600/69540509/5896cc3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Wallkill [](https://www.expedia.ca/Wallkill-Hotels-Rustic-And-Cozy-Geodesic-Dome-In-The-Woods-1.h69540509.Hotel-Information) 9.8/10 Exceptional (14 reviews) "My wife, dog & I had a great time away. Can’t wait to go back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew G. CA $347 CA $575 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Wallkill-Hotels-Rustic-And-Cozy-Geodesic-Dome-In-The-Woods-1.h69540509.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-29&endDate=2026-01-30®ionId=6046665&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=APART_HOTEL) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=VACATION_HOME) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=APARTMENT) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=COTTAGE) Condos [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=CONDO) Villas [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=VILLA) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=CHALET) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Private-Vacation-Homes.d6046665-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Private-Vacation-Homes.d6046665-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![DoubleTree by Hilton Hotel Nanuet](https://images.trvl-media.com/lodging/1000000/10000/800/736/w3839h2556x0y3-9a7a26d9_y.jpg) ### DoubleTree by Hilton Hotel Nanuet 10/10 Excellent "Staff was awesome. Room was great. Pool and hot tub very clean. Hot tub didn’t feel disgusting like a lot of places. " [](https://expedia.ca/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.Hotel-Information) ![Crowne Plaza Suffern - Mahwah by IHG](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/e31233cf_y.jpg) ### Crowne Plaza Suffern - Mahwah by IHG 10/10 Excellent "Great staff and clean room. " [](https://expedia.ca/Nyack-Hotels-Crowne-Plaza-Suffern-Mahwah.h2358.Hotel-Information) ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b_y.jpg) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 10/10 Excellent "Good stay" [](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Mountain Creek](https://images.trvl-media.com/lodging/3000000/2900000/2899900/2899900/f09dc021_y.jpg) ### Mountain Creek 10/10 Excellent "easy check-in/check-out" [](https://expedia.ca/Vernon-Hotels-Mountain-Creek.h2899900.Hotel-Information) ![Overlook Lodge at Bear Mountain](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6_y.jpg) ### Overlook Lodge at Bear Mountain 10/10 Excellent "Cozy and quiet. Rooms need size. Surroundings idellic. Nature abounds." [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Homewood Suites by Hilton Mahwah](https://images.trvl-media.com/lodging/1000000/700000/699300/699247/85ff4dc1_y.jpg) ### Homewood Suites by Hilton Mahwah 10/10 Excellent "Clean room, comfortable bed, accommodated all of our needs. " [](https://expedia.ca/Mahwah-Hotels-Homewood-Suites-By-Hilton-Mahwah.h699247.Hotel-Information) ![Super 8 by Wyndham Mahwah](https://images.trvl-media.com/lodging/1000000/10000/1200/1157/d1eaddcb_y.jpg) ### Super 8 by Wyndham Mahwah 10/10 Excellent "Clean and daily bed was made" [](https://expedia.ca/Mahwah-Hotels-Super-8-By-Wyndham-Mahwah.h1157.Hotel-Information) ![Hampton Inn by Hilton Middletown](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/8c9a3fbd_y.jpg) ### Hampton Inn by Hilton Middletown 10/10 Excellent "Great staffing, clean rooms!!!" [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information) ![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e_y.jpg) ### Holiday Inn Express Hotel & Suites Chester by IHG 10/10 Excellent "Yanki was very helpful , attentive and friendly. The breakfast was lousy ! It was the same thing every day . They had coffee and tea available. Parking was easy . Clean room . " [](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ## Find out more about Chester ## Chester Vacation Homes information | Number of reviews | 281 | | ----------------- | ------------------ | | Accommodation | 326 Vacation Homes | | Lowest Price | CA $213 | | Highest Price | CA $1,267 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [2 Star Hotels in Harriman ](https://www.expedia.ca/2Star-Harriman-Hotels.s20-0-d183682.Travel-Guide-Filter-Hotels) - [Hotels near Arrow Park Lake and Lodge ](https://www.expedia.ca/Arrow-Park-Lake-And-Lodge-Hotels.0-l6209262-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Blooming Grove ](https://www.expedia.ca/Blooming-Grove-Hotels-Cheap-Hotels.0-0-d3000448042-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Blooming Grove ](https://www.expedia.ca/Blooming-Grove-Hotels-Hotels-With-Free-Breakfast.0-0-d3000448042-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - 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