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Compare 1,151 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Our top choices for Cheshire hotels

Hyatt Place Milford / New Haven

3.0 star property
8.6 out of 10, Excellent, (1092)
"Late night check-in, gracious staff and great hot breakfast. "
The price is CA $153
CA $176 total
includes taxes & fees
Sep 1 - Sep 2
Hyatt Place Milford / New Haven

Homewood Suites by Hilton Orange New Haven

3.0 star property
9.2 out of 10, Wonderful, (951)
"Clean place with great amenities like a pool, gym, laundry service, breakfast buffet."
The price is CA $196
CA $225 total
includes taxes & fees
Aug 28 - Aug 29
Homewood Suites by Hilton Orange New Haven

Delamar West Hartford

4.0 star property
9.8 out of 10, Exceptional, (1001)
"Beautiful hotel, safe area, walk to shopping and restaurants. The staff was extremely nice and accommodating."
The price is CA $508
CA $605 total
includes taxes & fees
Sep 7 - Sep 8
Delamar West Hartford

Cheshire Welcome Inn

2.5 star property
8.4 out of 10, Very good, (721)
"The professionalism and the courtesy was excellent. The staff is friendly, welcoming and professional."
The price is CA $136
CA $156 total
includes taxes & fees
Aug 25 - Aug 26
Cheshire Welcome Inn

Atlantic Inn

3.0 star property
9.4 out of 10, Exceptional, (480)
"Wonderful, old school, motel. Clean, neat, great innkeeper & an easy walk to everything in town!"
The price is CA $192
CA $221 total
includes taxes & fees
Aug 25 - Aug 26
Atlantic Inn

Howard Johnson by Wyndham Hartford South – Rocky Hill

2.0 star property
8.2 out of 10, Very good, (1001)
"Easy check in, clean and spacious room, close to restaurants and other necessities. "
The price is CA $123
CA $142 total
includes taxes & fees
Aug 25 - Aug 26
Howard Johnson by Wyndham Hartford South – Rocky Hill

Comfort Inn & Suites Meriden East

2.5 star property
7.2 out of 10, Good, (1001)
"I liked everything I would definitely come back and the food is so good "
The price is CA $125
CA $144 total
includes taxes & fees
Sep 1 - Sep 2
Comfort Inn & Suites Meriden East

Holiday Inn Express Southington by IHG

2.5 star property
8.8 out of 10, Excellent, (1067)
"Great stay"
The price is CA $144
CA $165 total
includes taxes & fees
Sep 21 - Sep 22
Holiday Inn Express Southington by IHG

Homewood Suites by Hilton Wallingford-Meriden

3.0 star property
9.0 out of 10, Wonderful, (859)
"Needs some updating but clean, comfortable bed, breakfast was good! "
The price is CA $182
CA $210 total
includes taxes & fees
Aug 31 - Sep 1
Homewood Suites by Hilton Wallingford-Meriden

American Inn

2.0 star property
8.0 out of 10, Very good, (459)
"Great place to stay and clean. "
The price is CA $120
CA $139 total
includes taxes & fees
Aug 26 - Aug 27
American Inn

Holiday Inn Express Branford-New Haven by IHG

3.0 star property
8.8 out of 10, Excellent, (1003)
"Would stay here again "
The price is CA $152
CA $175 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express Branford-New Haven by IHG

Hyatt House Shelton

3.0 star property
8.4 out of 10, Very good, (1002)
"Food and bed were great."
The price is CA $165
CA $189 total
includes taxes & fees
Aug 31 - Sep 1
Hyatt House Shelton

Hampton Inn Milford

2.5 star property
8.0 out of 10, Very good, (1002)
"Convenient location from I-95, friendly desk staff, easy check-in & check-out."
The price is CA $134
CA $154 total
includes taxes & fees
Aug 31 - Sep 1
Hampton Inn Milford

Inn at Middletown

3.5 star property
9.0 out of 10, Wonderful, (498)
"Charming hotel conveniently located in walkable Middletown"
The price is CA $254
CA $320 total
includes taxes & fees
Aug 25 - Aug 26
Inn at Middletown

Solano Inn

2.5 star property
9.0 out of 10, Wonderful, (176)
"Spacious hotel clean and convenient with the event we had , close distance from "
The price is CA $134
CA $154 total
includes taxes & fees
Aug 25 - Aug 26
Solano Inn

Holiday Inn Express & Suites Meriden by IHG

2.5 star property
8.2 out of 10, Very good, (1003)
"Great Amenities and Fresh Coffee."
The price is CA $152
CA $175 total
includes taxes & fees
Sep 11 - Sep 12
Holiday Inn Express & Suites Meriden by IHG

Spark by Hilton Guilford

2.5 star property
8.2 out of 10, Very good, (21)
"Friendly and helpful staff Great area"
The price is CA $175
CA $201 total
includes taxes & fees
Aug 31 - Sep 1
Spark by Hilton Guilford

Courtyard New Haven Wallingford

3.0 star property
8.8 out of 10, Excellent, (760)
"It was a nice place to stay. "
The price is CA $187
CA $215 total
includes taxes & fees
Aug 31 - Sep 1
Courtyard New Haven Wallingford

Days Inn by Wyndham Southington

2.0 star property
7.2 out of 10, Good, (1003)
"I really like the place everything was good , nice area convenient, restaurants nearby,easy check in,I recommend it "
The price is CA $123
CA $142 total
includes taxes & fees
Aug 25 - Aug 26
Days Inn by Wyndham Southington

Best Western Executive Hotel Of New Haven - West Haven

2.5 star property
7.8 out of 10, Good, (1306)
"Staff was very friendly and knowledgeable of the area."
The price is CA $145
CA $167 total
includes taxes & fees
Aug 31 - Sep 1
Best Western Executive Hotel Of New Haven - West Haven
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.
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Learn more about Cheshire

Hikers and nature lovers flock to Cheshire's Farmington Canal Heritage Trail, where paved paths wind through scenic forests and historic landmarks. Families enjoy cooling off at Mixville Recreation Area's swimming pond in summer, while the annual Strawberry Festival offers local treats and community charm.

Photo by Tai Bui
Open Photo by Tai Bui

Stay near popular Cheshire attractions

Find out more about Cheshire

Find out more about Cheshire

Top reasons to visit Cheshire

  • Charming Heart of Cheshire: Explore historic sites and enjoy the scenic beauty in the delightful Heart of Cheshire, perfect for leisurely strolls.
  • Outdoor Adventures: Embark on the Cheshire Sandstone Trail for hiking and other outdoor activities amidst beautiful landscapes.
  • Cultural Experiences: Visit local art galleries and historic colleges, immersing yourself in the rich culture of the area.
  • Family-Friendly Activities: Enjoy family-oriented attractions, including nearby theme parks and urban parks.
  • Diverse Accommodation Options: Find a range of hotels from budget-friendly to upscale, ensuring a comfortable stay.

Find great hotels in Cheshire

Cheshire, Connecticut, offers a diverse selection of hotels to suit all budgets and preferences, ranging from 2 to 4 stars. Whether you're seeking a comfortable family getaway, a pet-friendly retreat, or facilities tailored for business travellers, you'll find plenty of options. Discover the best hotels in Cheshire that promise a memorable stay, combining convenience with warm hospitality.

  • Courtyard by Marriott Waterbury Downtown: This 3-star hotel offers a vibrant and modern atmosphere just 11.3km from Cheshire. Perfect for adventurous travellers, the Courtyard by Marriott provides a host of recreational activities nearby, including hiking, mountain biking, and skiing. Guests can indulge in a delicious cooked breakfast, as well as enjoy the on-site bar and lounge. With amenities such as a 24-hour fitness facility and entertainment options like satellite and flat-screen TVs, this hotel ensures a comfortable stay. Its convenient location near various attractions, including shopping districts and theme parks, makes it an excellent choice for those seeking both relaxation and excitement.
  • Clarion Inn: Located 12.9km from Cheshire, the Clarion Inn is ideal for business travellers and pet lovers alike. This 3-star hotel boasts multiple meeting rooms and conference spaces, making it perfect for corporate events. Its pet-friendly policies allow dogs and cats, ensuring that your furry companions can join you on your travels. Guests appreciate the friendly service and comfortable accommodations, while amenities designed for business convenience enhance the overall experience. The Clarion Inn is a welcoming retreat for those balancing work and leisure.
  • Red Roof Inn Hartford - New Britain: Situated 20.9km from Cheshire, the Red Roof Inn Hartford - New Britain is a family-friendly and pet-friendly choice. This hotel offers a warm atmosphere, featuring child-friendly amenities such as window guards and free cribs, making it a great pick for families. Pets are also welcome, with a flexible policy that includes dogs and cats. The hotel caters to a range of needs, ensuring a pleasant stay for guests travelling with children and pets. With its focus on family comfort and accommodating services, this inn is a convenient option for budget-conscious travellers.

Where to stay in Cheshire

Cheshire, Connecticut, offers a delightful blend of family-friendly activities and rich cultural experiences. Visitors can explore the charming Heart of Cheshire, where historic sites beckon, while enjoying the scenic beauty of the surrounding areas. With its ideal central location, Cheshire serves as a perfect base for day trips to nearby towns like historic Chester, ensuring a memorable vacation filled with friendly locals and picturesque landscapes.

  • Meriden: Located 9.7km from Cheshire, Meriden offers a rich blend of family-friendly activities and cultural experiences. This city attracts visitors year-round, with peak seasons in April, July, and September. Here, you can explore educational venues, enjoy live performances at the theatre, or try your luck at the local casino. Notable landmarks include a historic college university and a popular theme park, making it a great destination for family outings.
  • Waterbury: Just 12.9km away from Cheshire, Waterbury is a vibrant city perfect for adventure seekers and outdoor enthusiasts. Visitor numbers peak in April and during the summer months of June and July, ensuring a lively atmosphere. In Waterbury, you can access exciting activities such as waterparks and resorts, alongside educational institutions and casinos. The city is home to significant attractions like an event conference venue and a thrilling theme park, making it an excellent spot for family adventures.
  • Wallingford: Situated 9.7km from Cheshire, Wallingford is known for its cultural richness and romantic charm. With a steady stream of visitors throughout the year, peak times occur in April, July, and September. This city offers a variety of activities, including theatre performances and casino experiences. Key attractions include historic colleges and a modern university, alongside event venues that host various activities, making Wallingford a delightful place to explore for families and couples alike.

Things to do in Cheshire

Cheshire, Connecticut, offers a delightful mix of family-friendly activities and cultural experiences. Enjoy a relaxing spa break, explore local art galleries, and embark on the Cheshire Sandstone Trail for outdoor adventures. Thrill-seekers can visit nearby theme parks, while shopping enthusiasts will appreciate the charming stores. This charming town is perfect for a memorable vacation filled with fun and exploration.

Shopping

For shopping in Cheshire, visit Maplecroft Plaza Shopping Center for a family-friendly vibe. Amity Village Shopping Center, only 9.7km away, offers entertainment and city atmosphere. Brass Mill Center, located 11.3km from Cheshire, is perfect for family fun and business shopping. If you're up for a drive, explore more options nearby!

Recreation

Hubbard Park offers a peaceful retreat with scenic walking trails and tranquil gardens, perfect for relaxation. The Cheshire Golf Course invites you to enjoy a round of golf amidst beautiful landscapes, while Falcon Field provides energetic sports events and activities, fostering a lively community atmosphere.

Adventure

At Powder Ridge Mountain Park and Resort, experience thrilling skiing and snowboarding on diverse slopes located 14.5km from Cheshire. For karting enthusiasts, Checkered Flag Raceway offers an adrenaline-pumping ride 17.7km away. Hike the scenic trails of Shade Swamp Sanctuary, situated 22.5km away, for a refreshing outdoor adventure.

Nightlife

Experience the vibrant nightlife in Cheshire with a show at the Toyota Oakdale Theatre, just 8.0km away, offering a blend of culture and romance. For family fun, visit Crystal Bees, 14.5km away, or admire the stars at the Van Vleck Observatory, located 20.9km from town.

Booking tips and Expedia advantages for Cheshire

To save money on your trip to Cheshire, visit popular free attractions like Quinnipiac University and Choate Rosemary Hall. Consider travelling between December and February for lower accommodation rates, as hotel prices rise in May, June, and October. Book your stay on a Tuesday for the best rates, and use Expedia's search tool to find budget-friendly options by filtering prices from lowest to highest. Combine your hotel, flights, and activities for additional savings. Look for special deals on cheap hotels to maximize your budget during your visit.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Cheshire are December to February, where the prices are slightly lower. This is in comparison to May to June and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Cheshire is Tuesday. The most expensive day to stay in Cheshire is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia's search tool to refine your preferences, including your budget, desired location, and preferred hotel type. To find the most affordable options and special offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel booking in Cheshire with your flights and activities through an Expedia package.

Find the best attractions in Cheshire

Cheshire, Connecticut, offers a perfect blend of family-friendly activities, cultural experiences, and outdoor adventures. Visitors can explore historic colleges and universities, relax in urban parks, and enjoy the beauty of national and state parks. This charming town caters to a variety of interests, making it an ideal destination for travellers seeking a memorable vacation filled with exploration and enjoyment.

  • Quinnipiac University: Located 9.7km from Cheshire, this historic university offers a rich cultural experience with beautiful architecture and vibrant campus life, perfect for those who appreciate educational history.
  • Choate Rosemary Hall: Also 9.7km away, this modern college features impressive facilities and a dynamic atmosphere, providing a glimpse into contemporary educational innovations within a city-like vibe.
  • Lake Compounce: Situated 14.5km from Cheshire, this amusement park is a fantastic destination for families seeking adventure. Enjoy thrilling rides and outdoor activities in a fun-filled environment.

Best time to go to Cheshire

Visitor numbers in Cheshire is generally unchanged in popularity throughout the year. The best time to visit Cheshire is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January29.1°F (-1.6°C)Light RainMostly SunnyAverageSlightly Low
February30.7°F (-0.7°C)Light RainMostly CloudyAverageSlightly Low
March37.9°F (3.3°C)Light RainMostly SunnyAverageAverage
April48.7°F (9.3°C)Light RainMostly SunnySlightly HighAverage
May59.2°F (15.1°C)Light RainMostly SunnyAverageSlightly High
June67.5°F (19.7°C)Light RainMostly SunnySlightly HighSlightly High
July74.3°F (23.5°C)Light RainMostly SunnySlightly HighAverage
August72.7°F (22.6°C)Light RainMostly SunnyAverageAverage
September65.8°F (18.8°C)Light RainMostly SunnyAverageAverage
October55.0°F (12.8°C)Light RainMostly SunnySlightly LowSlightly High
November43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage
December35.4°F (1.9°C)Light RainMostly SunnySlightly LowSlightly Low

The nearest major airports for your trip to Cheshire

When visiting Cheshire, Connecticut, the most convenient airports are Hartford, CT (BDL-Bradley Intl.) located 49.9km away, and White Plains, NY (HPN-Westchester County) and Islip, NY (ISP-MacArthur) both situated 82.1km away. Near Hartford, consider staying at the DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport, or the Simsbury 1820 House, 11.3km away. For White Plains, the 5-star Opus Westchester is 6.4km from HPN. Islip offers the Hyatt Regency Long Island, also 6.4km from ISP. All hotels provide accessible transportation options to their respective airports.

Frequently asked questions

What's the best place for a stay in Cheshire?

Based on Expedia's traveler preferences, Cheshire Welcome Inn is a top place to stay in Cheshire. Other good choices for your stay in the area are The Capitol Hotel and Best Western Executive Hotel Of New Haven - West Haven. See all available top hotels, or vacation rentals in Cheshire.

What are some of the best vacation rentals in Cheshire?

Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views: This vacation home rental outside of Cheshire is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. See all vacation rentals in Cheshire.

If I need to cancel my hotel reservation in Cheshire, will I receive a refund?

Yes, most hotel room reservations are refundable if you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before your arrival date. If you have a non-refundable reservation, it might still be possible to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Cheshire.

Where can I learn more about changing or cancelling my trip to Cheshire?

For more information about changing or cancelling your trip to Cheshire, click here.

What is the top LGBTQ-friendly hotel in Cheshire?

Holiday Inn Cheshire - Southington by IHG is a top LGBTQ-friendly hotel, and features free WiFi and sofa beds. See all available hotels listed as LGBTQ-friendly in Cheshire.

Where is the best hotel to stay near Barker Museum?

Holiday Inn Cheshire - Southington, an IHG Hotel is one of the top choices for your stay based on our traveler data, and this 3-star hotel offers a restaurant and an indoor pool. It's located 2.3 mi (3.6 km) from Barker Museum. Other good options within 5 miles include Econo Lodge Milldale - Southington and Cheshire Welcome Inn.

What about the best place to stay near Cheshire Hollow Farm?

One of the top choices for your stay is Holiday Inn Cheshire - Southington, an IHG Hotel, located 1 mi (1.7 km) from Cheshire Hollow Farm, and this 3-star hotel offers a restaurant and an indoor pool. Econo Lodge Milldale - Southington and Homewood Suites by Hilton Southington, CT are two other good options within 5 miles.

What are some accommodations with pools in Cheshire?

Holiday Inn Cheshire - Southington by IHG: Offers a snack bar/deli, an indoor pool, and free self parking. Hampton Inn & Suites Hartford/East Hartford and Best Western Executive Hotel Of New Haven - West Haven are a couple of other choices with an onsite pool. View all hotels with pools in Cheshire.

What's the best place to stay near Tweed - New Haven Regional Airport (HVN)?

Quality Inn East Haven - New Haven is a popular hotel, featuring free breakfast and free WiFi. It's located a short 1.3 mi (2.1 km) from Tweed - New Haven Regional Airport. Other good options close to the airport include La Quinta Inn & Suites by Wyndham New Haven and Omni New Haven Hotel at Yale.

How is it to stay in Cheshire?

Visitors to Cheshire are sure to enjoy the restaurants. Tourists can also enjoy the city's waterfalls and shopping. In Cheshire, there are 4 hotels and other accommodations to choose from. Find out more about Cheshire.

What is there to see in Cheshire?

Favorite family attractions include Barker Character, Comic and Cartoon Museum and Cheshire Hollow Farm. Natural beauty is on display at Drazen Orchards, Bartlem Park, and Roaring Brook Park. A couple of additional sights to add to your agenda are Maplecroft Plaza Shopping Center and Lock 12 Historical Park. Check out what more to see and do in Expedia's Cheshire guide.

What's the seasonal weather like in Cheshire?

The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 33°F. Average annual precipitation for Cheshire is 54 inches.