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Find Hotels with a Pool in Winchester, CT from CA $178

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Check availability on Winchester Hotels with a Pool

Tonight
Sep 28 - Sep 29
Tomorrow
Sep 29 - Sep 30
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Winchester hotels with a pool

An outdoor patio with wicker furniture and a small table, surrounded by a garden and trees.
A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.
A bathroom with a toilet, sink, bathtub, and a glass-enclosed shower.
A grand hallway with a chandelier, a staircase, and a table with flowers.

1. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
CA $178
CA $205 total
includes taxes & fees
Oct 27 - Oct 28
Blackberry River Inn
A large indoor swimming pool with multiple seating areas and large windows.
A modern breakfast area with a counter, seating, and a refrigerator.
A modern hotel building with multiple floors and a prominent "HOME 2 SUITES BY HILTON" sign.
A modern lounge with a pool table, comfortable seating, and a large window offering a view of the outdoors.

2. Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
Bristol
  • Serene hotel with an indoor pool escape just steps away from relaxing in a soothing hot tub.
CA $184
CA $212 total
includes taxes & fees
Oct 4 - Oct 5
Home2 Suites by Hilton Bristol
A swimming pool with lounge chairs and a covered seating area, surrounded by multi-story buildings with visible windows and a brick facade.
A stone fireplace with a flat-screen TV above it, surrounded by two chairs and a small table.
A Marriott hotel with a red roof, a swimming pool, and a well-maintained lawn.
An outdoor patio with a circular fire pit surrounded by wicker chairs, a grill, and a dining area with tables and chairs.

3. Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
Avon
  • Splash into mountain adventures with a rejuvenating seasonal outdoor pool and hot tub retreat just steps from scenic trails.
CA $203
CA $234 total
includes taxes & fees
Oct 4 - Oct 5
Residence Inn by Marriott Hartford Avon
A large, historic building with a covered porch and outdoor seating area.
A large, historic house with multiple chimneys, a covered porch, and lush greenery.
A sign for the Simsbury House, indicating it is a historic building from 1820.
A grand staircase with patterned carpet, a wooden table with a vase of flowers, a chandelier, and a clock.

4. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
  • Dive into an indoor pool oasis year-round at this charming Simsbury bed and breakfast.
CA $267
CA $332 total
includes taxes & fees
Sep 29 - Sep 30
Simsbury 1820 House
A swimming pool with lounge chairs and umbrellas, surrounded by a house and trees.
A conservatory with a glass ceiling, round tables, and chairs, and a brick wall with an exit sign.
A spacious indoor dining area with high ceilings, large windows, and a brick wall.
A spacious lobby with a grand staircase, multiple seating areas, and a reception desk.

5. Avon Old Farms Hotel

Avon Old Farms Hotel
Avon
  • Dive into pure refreshment at this seasonal outdoor pool oasis with sauna and fitness centre.
CA $272
CA $344 total
includes taxes & fees
Oct 6 - Oct 7
Avon Old Farms Hotel
A backyard with a swimming pool, surrounded by lush greenery and a wooden deck.
A two-story building with a sign for Cornwall Inn, featuring a front porch and a mailbox.
A covered patio with a wooden table and chairs, a sofa, and a ceiling fan.
A dining area with wooden tables and chairs, large windows with white frames, and wall-mounted light fixtures.

6. Cornwall Inn and Lodge

Cornwall Inn and Lodge
Cornwall Bridge
  • Serene seasonal outdoor pool retreat nestled near Mohawk Mountain, where pool loungers and umbrellas invite summer relaxation.
CA $307
CA $353 total
includes taxes & fees
Sep 29 - Sep 30
Cornwall Inn and Lodge
An outdoor patio with wicker furniture, a glass-top table, and a barbecue grill.
A living room with a TV, leather sofas, a coffee table, and a small side table.
A bedroom with a bed, a nightstand, a lamp, a window with curtains, a television, and a bathroom door.
A two-story house with a dark gray exterior, a brick chimney, and a small front porch with a white railing.

7. Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
CA $165
CA $219 total
includes taxes & fees
Oct 5 - Oct 6
Collinsville River Escape / Fall Foliage, Deck & Yard
A rectangular swimming pool with a metal ladder, surrounded by a black metal fence.
A wooden deck with a swing chair and a bench overlooking a lake.
A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.
A modern hotel room with a bed, sofa, leather chair, and a small table.

8. Interlaken Inn & Resort

Interlaken Inn & Resort
Lakeville
  • Immerse in the sun-drenched seasonal outdoor pool surrounded by lush resort grounds and full-service spa amenities.
CA $282
CA $324 total
includes taxes & fees
Oct 26 - Oct 27
Interlaken Inn & Resort
A swimming pool with clear water, surrounded by a fence and trees.
A rustic bedroom with a large bed, wooden headboard, and a wooden floor. There is a chair and a small table with a lamp.
A lobby with a chandelier, a reception desk, and a sign indicating an exit.
A white building with a covered patio area, a brick chimney, and a garden with various plants and flowers.

9. The Litchfield Inn

The Litchfield Inn
Litchfield
CA $472
CA $543 total
includes taxes & fees
Sep 30 - Oct 1
The Litchfield Inn
An indoor swimming pool with clear blue water, surrounded by lounge chairs and large windows offering a view of greenery outside.
A hot tub with a metal ladder, surrounded by tiled walls, with a view of trees through a window.
A hotel with a prominent sign, a covered entrance, and a landscaped driveway.
A spacious lobby with high ceilings, a fireplace, comfortable seating, and a dining area with tables and chairs.

10. Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
Farmington
  • Swim and unwind at this stylish retreat where guests adore the indoor pool and hot tub for year-round aquatic relaxation.
CA $228
CA $263 total
includes taxes & fees
Oct 12 - Oct 13
Hampton Inn & Suites Hartford/Farmington
View all properties

Choose what matters most at hotels with a pool in Winchester

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Winchester Hotel Reviews

Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"We will be returning in May for our Anniversary. Very pleased with everything…"
Denise 2-night trip
Posted 3 days ago
Avon Old Farms Hotel
DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent
"Good location. Shuttle offered to wedding. Good venue for after party."
Katherine 2-night trip
Posted 10 days ago
DoubleTree by Hilton Hotel Bristol, Connecticut
Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent
"Everything was perfect—the room, the service, the restaurant, the spa; everything was perfect. An unforgettable experience."
Moshe 2-night trip
Posted 2 weeks ago
Mayflower Inn & Spa, Auberge Collection

Frequently asked questions

What are some hotels with pools in Winchester?
Enjoy a restful stay with fast internet, smart TV and the company of your pet.: Offers a snack bar/deli, an indoor pool, and buffet. Waterfront House & Guest House Available in Winchester, CT!: Provides a seasonal outdoor pool, an indoor pool, and a full-service spa. The Farmington Inn & Suites: Offers a sauna, a seasonal outdoor pool, and buffet. Extended Stay America Suites Hartford Farmington: Offers a snack bar/deli, an indoor pool, and free valet parking. Delamar West Hartford: Provides 2 bars, an indoor pool, and daily.
What is there to see and do in Winchester?
Make a point to visit attractions like Highland Lake and Laurel Lanes. During your stay, check out sights such as The Marina at Highland Lake, Burr Pond State Park, and Winchester Historical Society.
When is the best time to book a hotel with a pool in Winchester?
Taking into account the local weather in Winchester can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.

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