Chessy Resorts

House
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like-icon10.0
Exceptional
(9 Reviews)
1 Bedroom 1 Bath 6 Guests 753 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£106/Night 7 Nights - £742
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House
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
1 Bedroom 1 Bath 6 Guests 807.29 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£80/Night 7 Nights - £561
Bed & Breakfast
Map-icon
like-icon9.8
Exceptional
(108 Reviews)
1 Bedroom 1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£93/Night 7 Nights - £649
House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
1 Bedroom 1 Bath 2 Guests 474 ft²
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£94/Night 7 Nights - £659
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House
Map-icon
like-icon9.8
Exceptional
(56 Reviews)
1 Bedroom 1 Bath 2 Guests 538.2 ft²
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
More amenities
£123/Night 7 Nights - £862
House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
1 Bedroom 1 Bath 3 Guests 484 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
£62/Night 7 Nights - £435
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Apartment
like-icon9.8
Exceptional
(4 Reviews)
1 Bedroom 1 Bath 4 Guests 645.83 ft²
  • Parking
    Parking
  • Internet
    Internet
More amenities
£47/Night 7 Nights - £329
House
like-icon10.0
Exceptional
(1 Review)
2 Bedrooms 1 Bath 4 Guests 754 ft²
  • Balcony/Terrace
    Balcony/Terrace
  • Kitchen
    Kitchen
More amenities
£86/Night 7 Nights - £599
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Bed & Breakfast
Map-icon
like-icon9.7
Exceptional
(19 Reviews)
2 Bedrooms 1 Bath 2 Guests 161.46 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£92/Night 7 Nights - £642
Apartment
Map-icon
like-icon9.0
Exceptional
(2 Reviews)
1 Bedroom 1 Bath 4 Guests 431 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£91/Night 7 Nights - £640
star-icons-4
Bed & Breakfast
like-icon9.6
Exceptional
(141 Reviews)
2 Bedrooms 2 Baths 4 Guests 226.05 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£80/Night 7 Nights - £557
House
Map-icon
like-icon8.0
Excellent
(1 Review)
1 Bedroom 1 Bath 2 Guests 215 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£44/Night 7 Nights - £309

Why Choose Rent By Owner for your Chessy Resorts?

What makes our Resorts special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Weekly Weather Forecast for Chessy

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Other Places to Stay in Chessy

Frequently Asked Questions About Chessy Resorts

1. What are the top Resorts in Chessy?

There are a lot of options in Chessy. If you plan on staying in the Chessy area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Resorts in Chessy:

2. How many Resorts are available in Chessy?

Currently, the total number of properties listed by RBO in 2026 is over 100 in the Chessy area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Chessy. 

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  • Balcony/Terrace
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like-icon10.0
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  • Private Pool
    Private Pool
  • Fireplace/Heating
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More amenities
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  • Private Pool
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  • Fireplace/Heating
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3 Bedrooms 2 Baths 7 Guests 980 ft²
  • Balcony/Terrace
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  • Pet Friendly
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10 Bedrooms 9 Baths 29 Guests 4951 ft²
  • Fireplace/Heating
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like-icon10.0
Exceptional
(1 Review)
4 Bedrooms 2 Baths 13 Guests 1507 ft²
  • Balcony/Terrace
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  • Kitchen
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More amenities
£174/Night 7 Nights - £1,219