Windsor County Hotels with Pools

Select your dates to see hotels in Windsor County with a Pools for a refreshing stay.

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Amazing 9+Great 8+Good 7+Pleasant 6+

Best Windsor County Hotels with Swimming Pools

Check out our selection of Windsor County hotels with Pools

Most Booked

Lowest price

Closest to downtown

Highest Rated

99+

Jackson Gore Village on Okemo Mountain

Hotels in Ludlow

Featured facilities: Swimming Pool, Sauna, Massage Room

Very Good

101 reviews

8.5/10

1 night

From €153

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99+

Woodstock Inn & Resort

Hotels in Woodstock

Featured facilities: Swimming Pool, Bar, Spa

Great

101 reviews

9.3/10

1 night

From €884

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The Pointe at Castle Hill Resort & Spa

Hotels in Cavendish

Featured facilities: Swimming Pool, Spa, Massage Room

Very Good

101 reviews

8.6/10

1 night

From €151

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99+

Best Western Springfield Hotel

Hotels in Springfield

Featured facilities: Swimming Pool, Fitness Room

Very Good

101 reviews

8.7/10

1 night

From €191

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99+

On the River Inn

Hotels in Woodstock

Featured facilities: Swimming Pool, Bar, Spa

Great

103 reviews

9.1/10

1 night

From €142

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99+

Holiday Inn Club Vacations MOUNT ASCUTNEY RESORT by IHG

Hotels in Brownsville

Featured facilities: Swimming Pool, Bar, Fitness Room

Great

101 reviews

9.0/10

1 night

From €201

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Golden Stage Inn

Hotels in Cavendish

Featured facilities: Swimming Pool

Outstanding

30 reviews

10/10

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Castle Hill Resort Condo 5 Mi to Slopes at Okemo!

Hotels in Cavendish

Featured facilities: Swimming Pool, Spa, Fitness Room

Outstanding

5 reviews

10/10

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White River Inn & Suites

Hotels in White River Junction

Featured facilities: Swimming Pool

107 reviews

6.9/10

1 night

From €162

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Luxury 6Br Solitude Ge- Indoor Bball Court, Private Tub 6 Bedroom Home by Redawning

Hotels in Ludlow

Featured facilities: Swimming Pool, Fitness Room

Very Good

8.6/10

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See All Hotels with Pools in Windsor County

Frequently Asked Questions

What's the best hotel with Swimming Pools in Windsor County?

Whether your trip to Windsor County is for business or leisure, On the River Inn (from €156) , White River Inn & Suites (from €135) and Best Western Springfield Hotel (from €196) are popular choices.

What's the average price for hotels with Swimming Pools in Windsor County?

For hotels with Swimming Pools in Windsor County, the average price is €345 on weekdays and €425 on weekends (Friday–Saturday).

Which hotels with Swimming Pools in Windsor County have deals?

There are many deals available on Trip.com for both new and loyal users. Please check the promotions page to save your upcoming stays.

What's the best luxury hotel with Swimming Pools in Windsor County?

Windsor County has many luxury hotels with Swimming Pools. Woodstock Inn & Resort (from €1,098) is a popular option.