Title: Chester Vacation Rentals from $250: Search Short-Term Rentals | Expedia.com

[Chester Travel Guide](https://expedia.com/Chester.dx6046665)[Hotels in Chester](https://expedia.com/Chester-Hotels.d6046665.Travel-Guide-Hotels)[Flights to Chester](https://expedia.com/Cheap-Flights-To-Chester.d6046665.Travel-Guide-Flights)[Car Rentals in Chester](https://expedia.com/Car-Rentals-In-Chester.d6046665.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.com/Chester.d6046665.Destination-Travel-Guides)

![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

## Check prices for these dates

In two weeks

[Apr 10 - Apr 12](https://www.expedia.com/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.com/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.com/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.com/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/115000000/114370000/114369800/114369793/1d322732.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/115000000/114370000/114369800/114369793/18ffe7af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hike & Fish: Outdoor Retreat Near Trails

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

Westbrookville

$272 nightly

$308 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/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)

![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)

![Smart TV, books](https://images.trvl-media.com/lodging/83000000/82950000/82946400/82946328/fbf01887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/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.

$819 nightly

$855 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/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)

![Exterior](https://images.trvl-media.com/lodging/92000000/91200000/91196100/91196049/b03320b6.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)

![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)

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

[](https://www.expedia.com/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.

$963 nightly

$1,087 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/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)

![Interior](https://images.trvl-media.com/lodging/95000000/94860000/94859700/94859610/4e40d48d.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.com/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.

$469 nightly

$530 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/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)

![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)

![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/100000000/99760000/99751300/99751209/4246803e.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)

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

[](https://www.expedia.com/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.

$1,136 nightly

$1,296 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/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)

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/w1024h681x0y0-cfce0679.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/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.

$237 nightly

$280 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/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)

![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)

![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)

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

[](https://www.expedia.com/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

$492 nightly

$513 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/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)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/121000000/120020000/120015300/120015244/bc2d57e3.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)

![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)

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

[](https://www.expedia.com/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.

$278 nightly

$282 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/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)

![Dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/5ed95c10.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)

![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.com/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.

$270 nightly

$305 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/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)

![Smart TV, fireplace, foosball](https://images.trvl-media.com/lodging/31000000/30360000/30358400/30358356/5922982c.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)

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

[](https://www.expedia.com/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.

$484 nightly

$544 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/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)

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

![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.com/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.

$360 nightly

$412 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/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)

![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)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90900000/90899400/90899359/w1024h680x0y3-01a4cf5f.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)

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

[](https://www.expedia.com/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.

$237 nightly

$280 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/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/109000000/108780000/108777400/108777320/70357fc6.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)

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

[](https://www.expedia.com/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.

$407 nightly

$462 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/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)

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

![Smart TV, fireplace](https://images.trvl-media.com/lodging/74000000/73410000/73408100/73408065/786d651a.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.com/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.

$289 nightly

$327 total

Mar 26 - Mar 27

Total with taxes and fees

[](https://www.expedia.com/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)

![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)

![Interior](https://images.trvl-media.com/lodging/77000000/76010000/76007300/76007287/81f65114.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.com/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.

$1,122 nightly

$1,325 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/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)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110440000/110439100/110439036/ee891a06.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.com/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.

$629 nightly

$712 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/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)

![Smart TV](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/99922af1.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)

![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.com/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.

$442 nightly

$487 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/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)

![Dining](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w906h683x59y0-c6be118f.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.com/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.

$389 nightly

$440 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/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)

![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)

![Exterior](https://images.trvl-media.com/lodging/22000000/21770000/21763500/21763424/w1439h805x0y0-02bb0c77.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.com/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.

$479 nightly

$539 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/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)

![Property grounds](https://images.trvl-media.com/lodging/46000000/45750000/45742900/45742802/c225355f.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.com/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.

$267 nightly

$315 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/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.com/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

Cabins

[](https://www.expedia.com/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)

Private vacation homes

[](https://www.expedia.com/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)

Aparthotels

[](https://www.expedia.com/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)

Condos

[](https://www.expedia.com/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)

Apartments

[](https://www.expedia.com/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=APARTMENT)

Cottages

[](https://www.expedia.com/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)

Villas

[](https://www.expedia.com/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)

Chalets

[](https://www.expedia.com/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

![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.com/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.Hotel-Information)

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

### Hampton Inn & Suites Mahwah

10/10 Excellent

"Did not use "

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

![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

4/10 Poor

"I was highly disappointed. There was spitup on the bed rail and vents were extremely dirty. It's an older building too. There were cigarette stains on the dresser. No rooms were available to change and the housekeeper tired and clean but the presentation turned me off. "

[](https://expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Newburgh-Stewart-Airport.h42673.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.com/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.com/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.com/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.com/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.com/Nyack-Hotels-Hilton-Garden-Inn-Nanuet.h985904.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

"Was very clean and nice "

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

## Find out more about Chester

**Everything you need to know about Chester vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Chester vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $250 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Chester rentals**

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

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

## Frequently asked questions

### Are there vacation rentals in Chester?

### What are some of the best vacation home rentals in Chester?

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### What are vacation rentals like in Chester?

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- [Best Hotels in Ithaca](https://expedia.com/Ithaca-Hotels.d6056124.Travel-Guide-Hotels)
- [Best Hotels in Syracuse](https://expedia.com/Syracuse-Hotels.d601764.Travel-Guide-Hotels)
- [Niagara Falls Hotels with a View](https://expedia.com/Niagara-Falls-Hotels-Hotels-With-View.0-0-d602721-tHotelswithView.Travel-Guide-Filter-Hotels)
- [Best Hotels in Binghamton](https://expedia.com/Binghamton-Hotels.d6034018.Travel-Guide-Hotels)
- [Best Hotels in Lake George](https://expedia.com/Lake-George-Hotels.d6055969.Travel-Guide-Hotels)
- [Best Hotels in Rhinebeck](https://expedia.com/Rhinebeck-Hotels.d55927.Travel-Guide-Hotels)
- [Best Hotels in Poughkeepsie](https://expedia.com/Poughkeepsie-Hotels.d6056317.Travel-Guide-Hotels)
- [Best Hotels in Middletown](https://expedia.com/Middletown-Hotels.d8864.Travel-Guide-Hotels)
- [Best Hotels in Hudson](https://expedia.com/Hudson-Hotels.d55762.Travel-Guide-Hotels)
- [Best Hotels in Niagara Falls](https://expedia.com/Niagara-Falls-Hotels.d602721.Travel-Guide-Hotels)
- [Best Hotels in Cooperstown](https://expedia.com/Cooperstown-Hotels.d6487.Travel-Guide-Hotels)
- [Best Hotels in Yonkers](https://expedia.com/Yonkers-Hotels.d7789.Travel-Guide-Hotels)
- [Best Hotels in Utica](https://expedia.com/Utica-Hotels.d6055801.Travel-Guide-Hotels)

Flights

- [Flights to ALB](https://expedia.com/Cheap-Flights-To-Albany.d603260.Travel-Guide-Flights)
- [Flights to BUF](https://expedia.com/Cheap-Flights-To-Niagara-Falls.d602721.Travel-Guide-Flights)
- [Flights from Syracuse](https://expedia.com/lp/flights/601764/flights-from-syracuse)
- [Flights to SYR](https://expedia.com/Cheap-Flights-To-Syracuse.d601764.Travel-Guide-Flights)

Cars

- [Car rentals in Albany](https://expedia.com/Car-Rentals-In-Albany.d603260.Car-Rental-Guide)
- [Car rentals in Syracuse](https://expedia.com/Car-Rentals-In-Syracuse.d601764.Car-Rental-Guide)

Activities

- [Things to do in Niagara Falls](https://expedia.com/Things-To-Do-In-Niagara-Falls.d602721.Travel-Guide-Activities)

Packages

- [Niagara Falls Vacation Packages](https://expedia.com/Niagara-Falls.d602721.Destination-Travel-Guides)