Title: Chester Vacation Rentals from CA $343: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[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 two months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 17 - Jul 19](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-07-17&endDate=2026-07-19&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 rentals

![House (1 Bedroom) | Living area](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369793/780cac79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369793/d5ed89f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369793/a309408b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369793/18ffe7af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hike & Fish: Outdoor Retreat Near Trails

[](https://www.expedia.ca/Hike-Fish-Outdoor-Retreat-On-The-Basher-Kill.h114369793.Hotel-Information)

Westbrookville

CA $226

CA $422 total

includes taxes & fees

Apr 13 - Apr 14

[](https://www.expedia.ca/Hike-Fish-Outdoor-Retreat-On-The-Basher-Kill.h114369793.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/83000000/82950000/82946400/82946328/0a342993.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/83000000/82950000/82946400/82946328/8626ce26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/83000000/82950000/82946400/82946328/71847bf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/83000000/82950000/82946400/82946328/54e45e3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

[](https://www.expedia.ca/Goshen-Hotels-New-5-Bedrm3bath-Swim-Spa-Huge-Outdoor-Space.h82946328.Hotel-Information)

Goshen

10/10

Exceptional

(31 reviews)

"Home is very nicely furnished. Also, the backyard is great place to come and stargaze!! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elizabeth S.

CA $709

CA $1,173 total

includes taxes & fees

Apr 13 - Apr 14

[](https://www.expedia.ca/Goshen-Hotels-New-5-Bedrm3bath-Swim-Spa-Huge-Outdoor-Space.h82946328.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/92000000/91200000/91196100/91196049/f6544225.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/92000000/91200000/91196100/91196049/1ffadb78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/92000000/91200000/91196100/91196049/0864719a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91200000/91196100/91196049/w3093h1742x3y4-500f048d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ski House - ON THE SLOPE w/ hot tub

[](https://www.expedia.ca/Vernon-Hotels-Ski-House-ON-THE-SLOPE-W-Hot-Tub.h91196049.Hotel-Information)

Vernon Township

10/10

Exceptional

(20 reviews)

"Great location and great host."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rita L.

CA $1,070

CA $1,481 total

includes taxes & fees

Apr 13 - Apr 14

[](https://www.expedia.ca/Vernon-Hotels-Ski-House-ON-THE-SLOPE-W-Hot-Tub.h91196049.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/95000000/94860000/94859700/94859610/768f908e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/95000000/94860000/94859700/94859610/e3490481.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/95000000/94860000/94859700/94859610/5da89c64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/95000000/94860000/94859700/94859610/854fb559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern penthouse suite in a restored grain tower with private roof deck. 

[](https://www.expedia.ca/Warwick-Hotels-Modern-Penthouse-Suite-In-A-Restored-Grain-Tower-With-Private-Roof-Deck.h94859610.Hotel-Information)

Warwick

10/10

Exceptional

(27 reviews)

"Wonderful stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lisi M.

CA $463

CA $734 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Warwick-Hotels-Modern-Penthouse-Suite-In-A-Restored-Grain-Tower-With-Private-Roof-Deck.h94859610.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99760000/99751300/99751209/37d2f11c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/100000000/99760000/99751300/99751209/7a8f89cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/100000000/99760000/99751300/99751209/511279ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/100000000/99760000/99751300/99751209/20dd4d26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### New Farmhouse-Hot Tub, King Beds, Game Room & View

[](https://www.expedia.ca/Montgomery-Hotels-Dream-Escape.h99751209.Hotel-Information)

Montgomery

10/10

Exceptional

(16 reviews)

"We loved our stay here! The property is gorgeous and the hosts were helpful and communicative. The house was clean and had everything we needed."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Emily B.

CA $952

CA $1,731 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Montgomery-Hotels-Dream-Escape.h99751209.Hotel-Information)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/w1024h681x0y2-21ff539b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/w1024h680x0y3-d877abc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/w1024h680x0y3-8188dd85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/c421cfb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in the Heart of the Hudson Valley, Cabin 1

[](https://www.expedia.ca/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90897766.Hotel-Information)

Newburgh

10/10

Exceptional

(32 reviews)

"Great overnight spot, especially with a dog."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ed C.

CA $232

CA $387 total

includes taxes & fees

Apr 13 - Apr 14

[](https://www.expedia.ca/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90897766.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)

![Exterior](https://images.trvl-media.com/lodging/78000000/77290000/77280600/77280503/537494b9.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)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/78000000/77290000/77280600/77280503/d7a0c7a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Country House w/Hot Tub, Deck, Grill & Fire Pit

[](https://www.expedia.ca/Goshen-Hotels-Renovated-House-WHot-Tub.h77280503.Hotel-Information)

Goshen

10/10

Exceptional

(61 reviews)

"Very good host "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Binyomin

CA $355

CA $707 total

includes taxes & fees

Apr 13 - Apr 14

[](https://www.expedia.ca/Goshen-Hotels-Renovated-House-WHot-Tub.h77280503.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/121000000/120020000/120015300/120015244/01fd7250.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120020000/120015300/120015244/659c0b4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/121000000/120020000/120015300/120015244/ed92368d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/121000000/120020000/120015300/120015244/f115e0c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk to Mountain Creek Bike Park | Pool + Hot Tubs + Sauna

[](https://www.expedia.ca/Vernon-Hotels-Hike.h120015244.Hotel-Information)

Vernon Township

10/10

Exceptional

(46 reviews)

"Stacey was phenomenal! An excellent host. The rental was absolutely spotless and one of the coziest beds I've ever slept in, in my life. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ricardo S.

CA $209

CA $383 total

includes taxes & fees

Apr 13 - Apr 14

[](https://www.expedia.ca/Vernon-Hotels-Hike.h120015244.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/3a9ea66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/c55e3667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/e56d490f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/dfec5e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

[](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information)

Fort Montgomery

9.8/10

Exceptional

(133 reviews)

"Amazing place Thanks for the stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Julien C.

CA $258

CA $421 total

includes taxes & fees

Apr 13 - Apr 14

[](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information)

![Smart TV, fireplace, foosball](https://images.trvl-media.com/lodging/31000000/30360000/30358400/30358356/35f37461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/31000000/30360000/30358400/30358356/3fb5a88a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/31000000/30360000/30358400/30358356/f928e514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball](https://images.trvl-media.com/lodging/31000000/30360000/30358400/30358356/6cf6a2e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #248

[](https://www.expedia.ca/Vernon-Hotels-Appalachian-Mtn-Creek-Pool-Hot-Tubs-Sauna-Gym-Deck-Mtn-Front-248.h30358356.Hotel-Information)

Vernon

10/10

Exceptional

(12 reviews)

"Me, my partner and another couple stayed here for a summer weekend, the accommodations were so cozy, everything provided was great! The kitchen was fully equipped and we had pleasant breakfasts in the mornings, we went for the waterpark right around the corner, and we hope to return for the winter season. We all loved the stay! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

David C.

CA $332

CA $663 total

includes taxes & fees

Mar 30 - Mar 31

[](https://www.expedia.ca/Vernon-Hotels-Appalachian-Mtn-Creek-Pool-Hot-Tubs-Sauna-Gym-Deck-Mtn-Front-248.h30358356.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)

![Interior](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/d9fd7f11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/3745699f.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)

### Contemporary Cozy Cottage

[](https://www.expedia.ca/Lake-Peekskill-Hotels-Contemporary-Cozy-Cottage.h102145832.Hotel-Information)

Lake Peekskill

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 $309

CA $581 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Lake-Peekskill-Hotels-Contemporary-Cozy-Cottage.h102145832.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90900000/90899400/90899359/7ce45210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90900000/90899400/90899359/w1024h680x0y3-a5c935c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90900000/90899400/90899359/22854ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90900000/90899400/90899359/w1024h677x0y3-55eed7d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in the heart of the Hudson Valley, Cabin 3

[](https://www.expedia.ca/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90899359.Hotel-Information)

Newburgh

9.8/10

Exceptional

(14 reviews)

"We had a great stay, everything you need is provided. Would recommend to anyone."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bill W.

CA $232

CA $387 total

includes taxes & fees

Apr 13 - Apr 14

[](https://www.expedia.ca/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90899359.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108780000/108777400/108777320/w3379h2254x65y113-3bf6be6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108780000/108777400/108777320/w2205h3380x137y65-0561b2fe.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/109000000/108780000/108777400/108777320/w2352h3136x64y187-6f5dc167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/109000000/108780000/108777400/108777320/w3378h2246x65y117-b9d7217d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

[](https://www.expedia.ca/Vernon-Hotels-Luxe-10-Guest-Cottage-SkiGolfFire-PitLakesHike.h108777320.Hotel-Information)

Vernon Township

8.8/10

Excellent

(3 reviews)

"House was beautiful! Airy, cool and bedrooms were comfortable! Such a cute cottage and outdoor fire pit was amazing."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cherlyn I.

CA $309

CA $661 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Vernon-Hotels-Luxe-10-Guest-Cottage-SkiGolfFire-PitLakesHike.h108777320.Hotel-Information)

![Golf](https://images.trvl-media.com/lodging/74000000/73410000/73408100/73408065/w1224h825x0y4-1dc3d514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73410000/73408100/73408065/06263d52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/74000000/73410000/73408100/73408065/63736bb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/74000000/73410000/73408100/73408065/w1202h817x0y0-9676fa5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Two Full Baths in Newly Renovated ski golf Condo! New on Market!!

[](https://www.expedia.ca/Vernon-Hotels-Two-Full-Baths-In-Newly-Renovated-Ski-Golf-Condo-New-On-Market.h73408065.Hotel-Information)

Vernon Township

10/10

Exceptional

(33 reviews)

"Great time great location"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

R J.

CA $228

CA $450 total

includes taxes & fees

Apr 13 - Apr 14

[](https://www.expedia.ca/Vernon-Hotels-Two-Full-Baths-In-Newly-Renovated-Ski-Golf-Condo-New-On-Market.h73408065.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/77000000/76010000/76007300/76007287/4b55e569.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/77000000/76010000/76007300/76007287/20538ed5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76010000/76007300/76007287/d06f6457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/77000000/76010000/76007300/76007287/80caa095.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury School House Retreat With Sauna & Pool- 1HR from NYC

[](https://www.expedia.ca/New-Hampton-Hotels-Luxury-School-House-Wheated-Pool-1HR-From-NYC.h76007287.Hotel-Information)

New Hampton

10/10

Exceptional

(19 reviews)

"Home / "Old School House" was EXCEPTIONAL. Host is wonderful. We stayed for 6 nights and saw new items each day that we had not yet noticed. Owners have impeccable taste. Home has HUGE windows with wonderful Sunlight. I highly recommend this home. There were plenty of "local" restaurants in the nearby towns. Plenty of chain restaurants as well, but we prefer to eat local. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Felix F.

CA $1,050

CA $1,817 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/New-Hampton-Hotels-Luxury-School-House-Wheated-Pool-1HR-From-NYC.h76007287.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/111000000/110440000/110439100/110439036/f8f0e0fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/111000000/110440000/110439100/110439036/5591c9f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/111000000/110440000/110439100/110439036/w1021h680x3y3-4b98069e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/111000000/110440000/110439100/110439036/05db8e4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Entire Lakeview House \~ Hot Tub \~ Firepit \~ Stunning View \~ Spacious Deck

[](https://www.expedia.ca/Greenwood-Lake-Hotels-Luxury-Lake-Oasis-Hot-Tub-Lake-Marina-Views-Bar.h110439036.Hotel-Information)

Greenwood Lake

10/10

Exceptional

(7 reviews)

"We had lovely and relaxing stay at this property! The surrounding area is beautiful and the crowd are amazing!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Susan R.

CA $430

CA $982 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/Greenwood-Lake-Hotels-Luxury-Lake-Oasis-Hot-Tub-Lake-Marina-Views-Bar.h110439036.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/13d8fc7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/7dc21331_edited_faa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/99922af1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/0f1e7af8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk-to-Lake Cottage With Office for Quiet Days and Easy Work

[](https://www.expedia.ca/Putnam-Valley-Hotels-Walk-To-Lake-Cottage-With-Office-For-Quiet-Days-And-Easy-Work.h91391396.Hotel-Information)

Putnam Valley

9.8/10

Exceptional

(23 reviews)

"Great, clean house, nice accommodating host. Would stay here again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Heather T.

CA $229

CA $664 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Putnam-Valley-Hotels-Walk-To-Lake-Cottage-With-Office-For-Quiet-Days-And-Easy-Work.h91391396.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w506h683x259y0-6b740411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w919h683x47y0-1b7c08f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w905h683x60y0-1d21c342.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w506h683x259y0-81ebd497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hello Small Stone

[](https://www.expedia.ca/Middletown-Hotels-Hello-Small-Stone.h99261544.Hotel-Information)

Middletown

9.6/10

Exceptional

(5 reviews)

"The house was great. It was nice to sit and relax by the small pond in the back."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

John H.

CA $247

CA $610 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Middletown-Hotels-Hello-Small-Stone.h99261544.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/22000000/21770000/21763500/21763424/f587cc5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/22000000/21770000/21763500/21763424/w1439h805x0y0-02bb0c77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21770000/21763500/21763424/3271b2fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball](https://images.trvl-media.com/lodging/22000000/21770000/21763500/21763424/e4450407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #312

[](https://www.expedia.ca/Vernon-Hotels-Appalachian-Mtn-Creek-Pool-Hot-Tubs-Sauna-Gym-Deck-Mtn-Front-312.h21763424.Hotel-Information)

Vernon

9.6/10

Exceptional

(32 reviews)

"Loved our stay. Highly recommend and we’d definitely stay again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

John R.

CA $332

CA $657 total

includes taxes & fees

Mar 28 - Mar 29

[](https://www.expedia.ca/Vernon-Hotels-Appalachian-Mtn-Creek-Pool-Hot-Tubs-Sauna-Gym-Deck-Mtn-Front-312.h21763424.Hotel-Information)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/46000000/45750000/45742900/45742802/a27e5755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/46000000/45750000/45742900/45742802/5e31b747.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/46000000/45750000/45742900/45742802/03710a7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/46000000/45750000/45742900/45742802/41dec043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy country efficiency in the Hudson Valley

[](https://www.expedia.ca/Newburgh-Hotels-Cozy-Country-Efficiency-In-The-Hudson-Valley.h45742802.Hotel-Information)

Newburgh

9.8/10

Exceptional

(68 reviews)

"Clean, simple, and comfortable with clear host directions on arrival, checkin & checkout."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lou F.

CA $226

CA $436 total

includes taxes & fees

Apr 13 - Apr 14

[](https://www.expedia.ca/Newburgh-Hotels-Cozy-Country-Efficiency-In-The-Hudson-Valley.h45742802.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=2026-04-07&endDate=2026-04-08&regionId=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&regionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=APART_HOTEL)

Apartments

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Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America&regionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America&regionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=COTTAGE)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America&regionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=CABIN)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America&regionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=VILLA)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America&regionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=CONDO)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America&regionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=CHALET)

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## Top Chester Hotel Reviews

![Courtyard by Marriott Newburgh Stewart Airport](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/7494afa4_y.jpg)

### Courtyard by Marriott Newburgh Stewart Airport

6/10 Okay

"Older room with chemical cleaning solution smell"

[](https://expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Newburgh-Stewart-Airport.h42673.Hotel-Information)

![Hampton Inn & Suites Mahwah](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555820/c56a5aff_y.jpg)

### Hampton Inn & Suites Mahwah

6/10 Okay

"The staff when we came was not so pleased to help us "

[](https://expedia.ca/Mahwah-Hotels-Hampton-Inn-Suites-Mahwah.h3555820.Hotel-Information)

![Courtyard by Marriott Middletown Goshen](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/5a64b5a6_y.jpg)

### Courtyard by Marriott Middletown Goshen

10/10 Excellent

"Very clean "

[](https://expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information)

![Sonesta Simply Suites Nanuet](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/46d5cbe9_y.jpg)

### Sonesta Simply Suites Nanuet

10/10 Excellent

"Great Stay Would Definitely Stay Again"

[](https://expedia.ca/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.Hotel-Information)

![DoubleTree by Hilton Hotel Nanuet](https://images.trvl-media.com/lodging/1000000/10000/800/736/c532560d_y.jpg)

### DoubleTree by Hilton Hotel Nanuet

10/10 Excellent

"Everything was great. Customer service was genuine and welcoming!! "

[](https://expedia.ca/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.Hotel-Information)

![Spark by Hilton Fishkill](https://images.trvl-media.com/lodging/1000000/10000/2700/2642/b112328f_y.jpg)

### Spark by Hilton Fishkill

8/10 Good

"Overall my experience was good. I was hoping for more scrambled eggs and bacon. There was a homeless guy living in his car that was a bit nerve racking, but otherwise harmless. "

[](https://expedia.ca/Fishkill-Hotels-Spark-By-Hilton-Fishkill.h2642.Hotel-Information)

![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/8648b91b_y.jpg)

### Holiday Inn Express Hotel & Suites Chester by IHG

8/10 Good

"Parking was easy- lady at the front desk was great. Room was good "

[](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information)

![Hampton Inn Nanuet](https://images.trvl-media.com/lodging/2000000/1560000/1551400/1551336/f02832d4_y.jpg)

### Hampton Inn Nanuet

8/10 Good

"."

[](https://expedia.ca/Nyack-Hotels-Hampton-Inn-Nanuet.h1551336.Hotel-Information)

![Hilton Garden Inn Nanuet](https://images.trvl-media.com/lodging/1000000/990000/986000/985904/5d69e9ca_y.jpg)

### Hilton Garden Inn Nanuet

8/10 Good

"The front desk clerk was amazing when we checked in. The woman running the breakfast in the morning was pushy - pressuring us to buy the breakfast that we mistakenly thought was free. Overall, super convenient and clean. In the future, I'll be sure to pay a few extra bucks to add breakfast to our booking to avoid $15 for continental and $25 for a full breakfast (approx)."

[](https://expedia.ca/Nyack-Hotels-Hilton-Garden-Inn-Nanuet.h985904.Hotel-Information)

## Find out more about Chester

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Chester ](https://expedia.ca/Chester-Private-Vacation-Homes.d6046665-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Chester ](https://expedia.ca/Chester-Apartments.d6046665-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Chester ](https://expedia.ca/Chester-Cottages.d6046665-aaCottages.Travel-Guide-Accommodation)
- [Condo Rentals in Chester ](https://expedia.ca/Chester-Condos.d6046665-aaCondos.Travel-Guide-Accommodation)
- [Cabin Rentals in Chester ](https://expedia.ca/Chester-Cabins.d6046665-aaCabins.Travel-Guide-Accommodation)
- [Villas in Chester ](https://expedia.ca/Chester-Villas.d6046665-aaVillas.Travel-Guide-Accommodation)
- [Motels in Chester ](https://expedia.ca/Chester-Motels.d6046665-aaMotels.Travel-Guide-Accommodation)
- [B&B in Chester ](https://expedia.ca/Chester-Bed-And-Breakfast.d6046665-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Chalets in Chester ](https://expedia.ca/Chester-Chalets.d6046665-aaChalets.Travel-Guide-Accommodation)
- [Farmstay in Chester ](https://expedia.ca/Chester-Agritourism.d6046665-aaAgritourism.Travel-Guide-Accommodation)
- [Guest Houses in Chester ](https://expedia.ca/Chester-Guest-Houses.d6046665-aaGuestHouses.Travel-Guide-Accommodation)
- [RV Parks in Chester ](https://expedia.ca/Chester-RV-Parks.d6046665-aaRVParks.Travel-Guide-Accommodation)
- [Resorts in Chester ](https://expedia.ca/Chester-Resort-Hotels.d6046665-aaResortHotels.Travel-Guide-Accommodation)
- [Lodges in Chester ](https://expedia.ca/Chester-Lodges.d6046665-aaLodges.Travel-Guide-Accommodation)
- [Aparthotels in Chester ](https://expedia.ca/Chester-Apart-Hotels.d6046665-aaApartHotels.Travel-Guide-Accommodation)
- [Inns in Chester ](https://expedia.ca/Chester-Inns.d6046665-aaInns.Travel-Guide-Accommodation)

## Frequently asked questions

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