Romantic Wine Tours - Vacation Rentals in Chester

Incredible Ranch in the Woods - Peace and Luxury! From US $309
         

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10.0 (1 Review)
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Holiday Inn Express Hotel & Suites Chester by IHG From US $96
         

8.6 (1002 Reviews)
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Country House w/Hot Tub, Deck, Grill & Fire Pit From US $477
         

10.0 (59 Reviews)
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Spectacular Historic Mansion w/Pool&Tennis From US $3,504
         

10.0 (17 Reviews)
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Cozy studio on 36 acres close to everything in Warwick From US $211
         

10.0 (2 Reviews)
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Cozy cottage, beautiful views, close to Warwick! From US $243
         

Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space From US $573
         

9.8 (30 Reviews)
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Charming 1-bedroom Rekindled Farmhouse Historic Sugar Loaf, NY From US $197
         

9.8 (8 Reviews)
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Luxury Places to Stay in Chester

Over 50+ Luxury Places to Stay in or Near Chester
Private 5-Bed Country Estate on 22 Acres From US $3,442
         

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Secluded 9BR Getaway, Pool, Hot Tub & Huge Deck From US $1,992
         

Luxury 9BR Retreat w/Pool & Hot Tub From US $1,410
         

6.6 (4 Reviews)
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Elegant Home w/7BRs, Game Room, Luxury Yard, Pool From US $882
         

9.0 (2 Reviews)
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Summerville Getaway (30 min to Mt. Creek) From US $810
         

9.8 (16 Reviews)
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Spacious Smart Home Retreat on 14 Acres of Nature From US $699
         

7.4 (3 Reviews)
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Top-Rated Vacation Rentals with a Pool in Chester

Over 15+ Top-Rated Vacation Rentals with a Pool in or Near Chester
Holiday Inn Express Hotel & Suites Chester by IHG From US $346
         

8.3 (496 Reviews)
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Spacious 5-bedroom house with pool From US $765
         

10.0 (1 Review)
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Large 5-bedroom home on 3 acres From US $480
         

10.0 (1 Review)
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Spacious Home with Game Room and Pool From US $473
         

10.0 (1 Review)
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Secluded Spacious NY Getaway, 1 hour from NYC From US $1,206
         

8.8 (30 Reviews)
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Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard! From US $886
         

Charming Historic Farmhouse From US $350
         

4.8 (10 Reviews)
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Pet-Friendly Vacation Rentals in Chester

Over 17+ Pet-Friendly Vacation Rentals in or Near Chester
Luxury 9BR Retreat w/Pool & Hot Tub From US $1,833
         

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Awesome Country Retreat - 4BR - Private & Peaceful From US $388
         

7.4 (3 Reviews)
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Guesthouse 2 bedroom. 25min-West Point From US $183
         

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Very Private Large Home on 22 Acres with Outdoor Kitchennn From US $697
         

10.0 (1 Review)
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Awesome Country Retreat - 4BR - Private and Peaceful From US $419
         

9.8 (10 Reviews)
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Peace and Privacy at 5 BDRM Villa Set on Wooded Lot From US $559
         

9.6 (5 Reviews)
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  • Pet Friendly
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Luxury in the Woods, Pool, Privacy and Peace From US $564
         

9.0 (2 Reviews)
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Unique Scenic home with King suite & Hot tub From US $408
         

8.4 (11 Reviews)
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  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Chester on PetFriendly.io

Large Vacation Homes & Villas in Chester

Over 13+ Large Vacation Homes & Villas in or Near Chester
6 bedroom colonial house From US $332
         

8.6 (4 Reviews)
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Epic Cottage with Huge Garden - Sleeps 16! From US $298
         

3.8 (4 Reviews)
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  • TV
  • View
Pool, Fire Pit Bedroom & Alaska King – Sleeps 16 From US $745
         

Chester Varoom and Airbnb Places to Stay Under $200

Over 2+ Chester Varoom and Airbnb Places to Stay Under $200

Instantly Bookable Vacation Homes in Chester

Over 6+ Instantly Bookable Vacation Homes in or Near Chester
Charming 1-bedroom apartment with AC, WiFi in lovely Monroe
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From US $341
         

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4-bedroom house in delightful Chester with AC From US $508
         

Private fun From US $315
         

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Charming 1-bedroom apartment with AC, WiFi in lovely Monroe From US $232
         

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About Chester Vacation Rentals

With more than 59 Chester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Romanticwinetours and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Chester.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Romanticwinetours Chester, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Chester. Places to stay near Chester are 784.81 ft² on average, with prices averaging $764 a night.

Romanticwinetours makes it easy and safe to find and compare vacation rentals in Chester with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Chester

Type Count
Vacation Homes 34
Villas 13
Holiday Apartments 8
Hotels with Suites 2
Others 2

Use these Quick Filters to Find a Vacation Rental in Chester

Pro Tip: Romanticwinetours makes it easy to compare the best listings on Romanticwinetours homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Romanticwinetours homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chester.

Weather in Chester

View the weather forecast for Chester before booking your Chester Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F