A stone tower with a metal gate, surrounded by trees and a stone wall.

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Our top choices for Cheshire hotels

A spacious lobby with a sofa, armchairs, and a coffee table. There is a fireplace and a wall-mounted artwork.
A modern hotel lobby with a reception desk, a coffee station, and a store named "The Market" with various items on display.
A kitchen with wine bottles, glasses, and a chalkboard menu.
A modern kitchen with stainless steel appliances, wooden cabinets, and a wine display.

1. New Haven Hotel

New Haven Hotel
Downtown New Haven
United Kingdom
Hayley
$127 nightly
$146 total
Oct 27 - Oct 28
Total with taxes and fees
New Haven Hotel
A Holiday Inn hotel with a covered entrance and green lighting.
A modern restaurant with a wooden bar area, a long table with chairs, and a menu board.
An indoor swimming pool with a lifeguard warning sign, chairs, and a view of the outside.
A modern restaurant interior with a curved counter, seating area, and a wooden ceiling.

2. Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG
Southington
United States
Diana
$113 nightly
$130 total
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Cheshire - Southington by IHG
A hotel room with a large bed, a wooden nightstand, a TV, and a bathroom visible through an open door.
A coffee station with two coffee machines, a coffee press, and various coffee pods and cups.
A conference room with multiple tables and chairs, a whiteboard, and a projector screen.
A hotel room with a wooden desk, a chair, a flat-screen TV, a framed picture, and a window with curtains.

3. Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG
Southington
United States
Madhav
$93 nightly
$107 total
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Express Southington by IHG
A hotel lobby with a modern design, featuring a seating area with sofas, a fireplace, and a television mounted on the wall.
A hotel lobby with a seating area featuring sofas, armchairs, and ottomans.
A bar area with stools, shelves of beverages, and a coffee machine.
Restaurant

4. Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown
Waterbury
United States
Karen
$109 nightly
$125 total
Oct 12 - Oct 13
Total with taxes and fees
Courtyard by Marriott Waterbury Downtown
A dining area with tables and chairs, large windows with curtains, and a view of a cityscape.
A hotel room with two sofas, a coffee table, and a chair. There are large windows with curtains and a view of the city.
A spacious lobby with a central seating area, a chandelier, and wooden paneling.
A hotel room with a large bed, a television, a desk, and a view of the city.

5. Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale
Downtown New Haven
Canada
LARRY
$151 nightly
$174 total
Oct 27 - Oct 28
Total with taxes and fees
Omni New Haven Hotel at Yale
A hotel room with a bed, a sofa, a desk, a television, and a microwave.
A hotel entrance with a blue and white facade, a sign reading "BW Best Western," and two large planters with red flowers.
A modern lobby with a reception desk, a seating area, and a glass door entrance.
A modern hotel lobby with a sofa, coffee table, and a chandelier.

6. Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven
West Haven
United States
Zachary
$110 nightly
$126 total
Oct 11 - Oct 12
Total with taxes and fees
Best Western Executive Hotel Of New Haven - West Haven
A hotel room with a large bed, two bedside lamps, a desk with a chair, a large window with curtains, and an air conditioning unit.
A hotel room with two beds, a desk, and a view of a cityscape.
A beverage cooler with various drinks and a snack wall with assorted snacks and beverages.
A bathroom with a pedestal sink, a bathtub, a shower curtain, and a mirror with a towel rack.

7. The Capitol Hotel

The Capitol Hotel
Downtown Hartford
United States
Amy
$93 nightly
$107 total
Nov 1 - Nov 2
Total with taxes and fees
The Capitol Hotel
A landscaped garden with a large rock, yellow flowers, and a weeping willow tree.
A hotel room with two beds, a desk with a TV, a microwave, and a coffee maker.
A building with a sign indicating it is an AAA Approved office. There are trees and shrubs in front of the building.
A lobby with a leather sofa, a reception desk, framed pictures on the wall, and a door.

8. Cheshire Welcome Inn

Cheshire Welcome Inn
Cheshire
United States
Kerem
$97 nightly
$112 total
Nov 1 - Nov 2
Total with taxes and fees
Cheshire Welcome Inn
A modern lobby with seating, a dining area, and large windows.
An indoor swimming pool with clear blue water, surrounded by chairs and potted plants, and a high ceiling with recessed lighting.
A modern kitchen area with a central island, a coffee machine, and a sign that reads 'KITCHEN'.
A modern kitchen with a central island, bar seating, and a high ceiling with exposed beams.

9. Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North
North Haven
United States
Carol
$111 nightly
$128 total
Nov 1 - Nov 2
Total with taxes and fees
Clarion Inn North Haven - New Haven North
A modern hotel room with a red sofa, a small table, a TV, a dresser, and a window with a city view.
A hotel corridor with a tiled floor, a central door, and a seating area with chairs and a table.
A buffet setup with a geometric patterned wall, a fruit display, and various food items.
A reception area with two reception desks, a flat-screen TV, and a modern light fixture.

10. La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven
Long Wharf
United States
Kenneth
$117 nightly
$135 total
Nov 1 - Nov 2
Total with taxes and fees
La Quinta Inn & Suites by Wyndham New Haven
A hotel reception area with a stone wall backdrop, a reception desk, a blue armchair, and a patterned armchair.
A hotel room with a patterned sofa, a small table, two lamps, a chair, and a framed picture on the wall.
A lobby with a stone fireplace, a flat-screen TV, and two blue armchairs.
A hotel room with a large bed, two bedside lamps, a nightstand, and a window with curtains.

11. Hamden Hotel and Suites – Hamden New Haven

Hamden Hotel and Suites – Hamden New Haven
Hamden
United States
Janis
$99 nightly
$114 total
Nov 1 - Nov 2
Total with taxes and fees
Hamden Hotel and Suites – Hamden New Haven
A hotel lobby with a gray sofa, a round table, a reception desk, a TV, and a kitchen area in the background.
A Best Western Plus hotel with a two-story structure, multiple parking spaces, and a landscaped front yard.
A hotel room with a striped carpet, a desk with a lamp, a sofa, a small table, a nightstand with a lamp, and a bed.
A hotel room with a bed, bedside tables, a desk, a TV, a large mirror, a bathroom with a bathtub, and a striped carpet.

12. Best Western Plus New England Inn & Suites

Best Western Plus New England Inn & Suites
Berlin
United States
Dursun
$105 nightly
$120 total
Oct 25 - Oct 26
Total with taxes and fees
Best Western Plus New England Inn & Suites
An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled deck.
A Hilton Garden Inn with a covered entrance, landscaped gardens, and a clear sky.
A modern living room with a flat-screen TV, a red armchair, a grey sofa, a wooden entertainment unit, and a large window with curtains.
A hotel corridor with round tables, large windows, and a modern console table.

13. Hilton Garden Inn Wallingford/Meriden

Hilton Garden Inn Wallingford/Meriden
Wallingford
United States
Albert
$134 nightly
$155 total
Nov 1 - Nov 2
Total with taxes and fees
Hilton Garden Inn Wallingford/Meriden
A modern building entrance with a covered walkway, a white car parked in front, and two people near the entrance.
A modern bar area with a curved counter, bar stools, and a variety of bottles and glasses.
A spacious indoor area with multiple seating options, including sofas and round tables, and is well-lit with natural light from large windows.
A hotel room with a bed, a sofa, two armchairs, a small table, and a view of the water and city skyline.

14. Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton
Long Wharf
United States
Joseph
$117 nightly
$135 total
Oct 31 - Nov 1
Total with taxes and fees
Hotel Marcel New Haven, Tapestry Collection By Hilton
A modern kitchen with a central island, bar seating, and pendant lighting.
A modern living room with a large flat-screen TV, comfortable seating, and a bookshelf filled with books and decorative items.
A modern lounge area with a fireplace, seating arrangements, and a large window providing natural light.
A modern hotel building with a sign reading "CAMBRIA hotel" and a covered entrance labeled "CAMBRIA 12th".

15. Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area
West River
United States
Tanya
$114 nightly
$132 total
Oct 26 - Oct 27
Total with taxes and fees
Cambria Hotel New Haven University Area
A hotel lobby with a blue wall, a staircase, a brick planter, a patterned rug, and a bicycle.
Outdoor pool
A white brick building with a large window and a small garden with flowers.
Outdoor pool

16. The Circle Hotel Fairfield

The Circle Hotel Fairfield
Grasmere
United States
Greg
$151 nightly
$174 total
Nov 1 - Nov 2
Total with taxes and fees
The Circle Hotel Fairfield
An outdoor kitchen with a grill and a built-in stove, white chairs, and a red door.
A hotel room with a bed, a desk, a television, a sofa, and a window with a view of trees.
A multi-story hotel with a central entrance, a parking lot, and landscaped areas with shrubs and flowers.
A hotel lobby with a stone fireplace, multiple seating areas including a sofa and chairs, and a television mounted on the wall.

17. Homewood Suites by Hilton Wallingford-Meriden

Homewood Suites by Hilton Wallingford-Meriden
Wallingford
United States
Myriam
$149 nightly
$171 total
Nov 1 - Nov 2
Total with taxes and fees
Homewood Suites by Hilton Wallingford-Meriden
A bar area with a curved counter, bar stools, and a television screen above the bar.
A bar area with a curved counter, a refrigerated display case, and several wooden bar stools.
A hotel room with a sofa, a bed, a TV, and a desk with a telephone.
A lobby with a reception desk, seating area with sofas and chairs, and a decorative wall with a light fixture.

18. Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven
Milford
United States
Arlene
$118 nightly
$136 total
Oct 12 - Oct 13
Total with taxes and fees
Hyatt Place Milford / New Haven
A modern lobby with a stone wall, seating area, and a bar with bottles.
A spacious room with a wooden floor, large windows, and a chandelier.
A hotel room with a bed, bedside lamps, a TV, and a desk with drawers.
An indoor swimming pool with blue walls, a skylight, and lounge chairs.

19. Wyndham Southbury

Wyndham Southbury
Southbury
United States
Angela
$83 nightly
$96 total
Nov 1 - Nov 2
Total with taxes and fees
Wyndham Southbury
A hotel room with two beds, a desk with a computer, a TV, and artwork on the wall.
Two white front-loading washing machines in a laundry area with a white tiled wall and a red baseboard.
A rectangular pool with metal railings, surrounded by lounge chairs and a brick building with multiple windows and balconies.
A spacious lobby with a high ceiling, a chandelier, a fireplace, and a dining area with tables and chairs.

20. Days Inn by Wyndham Berlin Meriden

Days Inn by Wyndham Berlin Meriden
Berlin
United States
Faye
$68 nightly
$79 total
Nov 1 - Nov 2
Total with taxes and fees
Days Inn by Wyndham Berlin Meriden
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Where to stay in and around Cheshire

Cheshire offers a delightful mix of outdoor adventures and cultural experiences, perfect for family vacations. Explore the charming Cheshire city center and its friendly atmosphere, or venture into nearby districts for stunning scenery. High season attracts many business tourists, making it a vibrant spot for all travelers.
A cross and the words "Holy Land" on a hill.
Photo by Brandon Miller
A multi-tiered waterfall surrounded by autumn foliage.
A steel bridge over a calm river with autumn foliage.
A calm lake with a large rock in the center, surrounded by autumn-colored trees reflecting on the water's surface.
A park with a pond reflecting trees and a tall building.

Waterbury

Discover Waterbury, a vibrant city perfect for families and weekend getaways who will appreciate its blend of outdoor adventures and urban experiences. Visitors can enjoy thrilling rides at Lake Compounce amusement park, explore the historic architecture of Waterbury City Hall, and take in the academic atmosphere at Quinnipiac University. Located about 8 miles by car from Cheshire, Waterbury is a smart choice for those looking to book a hotel, with plenty of attractions to keep everyone entertained.

A town with a prominent church steeple, a main street, and surrounding greenery.
A calm river reflecting autumn foliage, surrounded by rocks and trees.
A mountainous landscape with dense forests, a small town, and a lake in the distance.
A snowy ski slope with skiers and snowboarders, ski lifts, and a forested area in the background.
A child sitting on a wooden bench with pumpkins and autumn leaves around.

Southington

Plan your stay in Southington, a top-rated choice for travelers looking for a delightful mix of family fun and outdoor adventure. This charming city is a mere 6 miles by car from Cheshire and offers attractions like the thrilling Lake Compounce amusement park, the educational Quinnipiac University, and the inviting Southington Public Library. With activities that appeal to both business visitors and families, Southington is an excellent choice for a memorable getaway.

A park with a paved walkway, trees, and a street lamp.
A town at dusk with illuminated streets and buildings, a prominent church steeple, and a crosswalk intersection.
A church with a tall spire, surrounded by trees and a stone bridge.
A red brick church with a white steeple and a clock tower, surrounded by trees and a paved street.
A forest with a clear path and scattered wooden stumps.
Photo by Bobby Bukes

Wallingford

Make your vacation planning effortless by staying in Wallingford, a haven for family travelers and weekend getaways due to its rich cultural experiences and proximity to Yale University and Choate Rosemary Hall. Visitors can enjoy outdoor adventures at Sleeping Giant State Park while being close to various entertainment options. Located about 6 miles by car from Cheshire, Wallingford offers a smart choice for your stay, blending convenience with a charming atmosphere.

A stone tower with American flags in front.
A stone tower surrounded by dense forest and rocky terrain.
A stone tower with a small entrance, surrounded by grass and rocks.
Photo by Marina Timo
A serene park with a reflective pond, lush trees, and a stone wall.
A waterfall cascading over moss-covered rocks.

Meriden

Meriden stands out as a prime spot for families and weekend getaway travelers interested in exploring Connecticut's rich cultural landscape and outdoor adventures. Visitors can enjoy attractions like the historic Wesleyan University and the modern Choate Rosemary Hall, as well as the thrilling rides at Lake Compounce amusement park. Ideally situated about 6 miles by car from Cheshire, Meriden offers easy access to these experiences, making it a smart choice for your next hotel booking.

A valley with autumn foliage, a river, and distant hills.

Prospect

Travelers visiting the area often choose Prospect as a base for their vacation, especially families and those looking for a weekend getaway. With attractions like the historic Yale University and the thrilling Lake Compounce amusement park, there's something for everyone to enjoy. Prospect's vibrant shopping areas and educational venues further enrich the experience. Located about 4 miles from Cheshire, this city offers easy access to local highlights, making it a smart choice for your stay.

Stay near popular attractions in and around Cheshire

Cheshire offers a delightful escape for families and culture enthusiasts alike. With its charming parks and expansive outdoor spaces, visitors can enjoy a variety of activities that celebrate nature and community. Discover the perfect blend of adventure and relaxation in this picturesque town.
A grassy hill with a stone wall and multiple tall metal structures.

Quinnipiac University

8.8/10 (244 reviews)
Set the stage for your exploration of Quinnipiac University, a historic college nestled in Hamden, Connecticut. With its vibrant cultural atmosphere, visitors can enjoy the campus's architecture and events. Located about 6 miles from Cheshire, it offers a convenient stop for those seeking to immerse themselves in local education and community life.
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A town surrounded by autumn foliage, with a prominent hill in the foreground.
Photo by Sanka Perera

Sleeping Giant State Park

8.8/10 (25 reviews)
An essential stop for outdoor lovers, Sleeping Giant State Park offers stunning scenery and adventure in Hamden, Connecticut. With its unique rock formations and extensive trails, visitors can immerse themselves in nature. Located about 5 miles from Cheshire, it’s a great base for exploring the area’s natural beauty.
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A waterfall surrounded by dense green foliage.

Roaring Brook Park

8.4/10 (12 reviews)
A must-see for families, Roaring Brook Park in Cheshire offers a delightful outdoor experience with its eco-friendly atmosphere and scenic beauty. Easily accessible, this park provides a perfect spot for relaxation and recreation, making it a convenient choice for those looking to explore the charm of the area.
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Choate Rosemary Hall

8.6/10 (22 reviews)
Often cited as a favorite for those interested in education and history, Choate Rosemary Hall offers a unique glimpse into a prestigious modern college experience. Located about 6 miles from Cheshire, its vibrant campus is perfect for a quick visit, making it easy to explore the surrounding area.
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Lake Compounce

8.0/10 (245 reviews)
Ideal for families seeking adventure, Lake Compounce offers thrilling rides and a beautiful outdoor setting. Located about 9 miles from Cheshire, this amusement park combines excitement with a scenic atmosphere, making it a convenient and enjoyable destination for your vacation.
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Mount Carmel

7.8/10 (17 reviews)
Considered a premier spot for outdoor enthusiasts, Mount Carmel in Hamden offers stunning scenery and a variety of adventurous trails. Located about 6 miles from Cheshire, it's an easy trek for those looking to immerse themselves in nature. Staying nearby allows for quick access to this beautiful mountain escape.
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Barker Character, Comic and Cartoon Museum

7.0/10 (12 reviews)
Enjoy the simplicity of a day filled with nostalgia at the Barker Character, Comic and Cartoon Museum in Cheshire, Connecticut, perfect for families seeking a fun cultural experience. Explore a vibrant collection of beloved characters and comics that will delight visitors of all ages. Staying near the museum makes it easy to immerse yourself in the charm of Cheshire.
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Mattatuck Beach

6.0/10 (1 review)
Perfectly suited for beach lovers, Mattatuck Beach offers a serene getaway with inviting beach vibes. Located about 4 miles by car from Cheshire, it provides easy access for a relaxing day under the sun. Staying near Mattatuck Beach ensures you can enjoy the beauty of the shore at your leisure.
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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.

See all hotels in Cheshire
A stone tower with a metal gate, surrounded by trees and a stone wall.

Top Cheshire Hotel Reviews

The Capitol Hotel

The Capitol Hotel

10/10 Excellent
"Yes"
hafz 1-night trip
Posted 15 hours ago
The Capitol Hotel
Hampton Inn & Suites New Haven - South - West Haven

Hampton Inn & Suites New Haven - South - West Haven

10/10 Excellent
"."
Loren 1-night trip
Posted 15 hours ago
Hampton Inn & Suites New Haven - South - West Haven
New Haven Hotel

New Haven Hotel

8/10 Good
"Very convenient location!"
Ray 1-night trip
Posted 15 hours ago
New Haven Hotel
Cheshire Welcome Inn

Cheshire Welcome Inn

10/10 Excellent
"La televisión no se pudo encender nunca, ni con el control ni manualmente. De ahi todo super 👌"
Brenda 1-night trip
Posted 15 hours ago
Cheshire Welcome Inn
Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton

10/10 Excellent
"Gorgeous restoration of a beautiful architectural gem."
Kenneth 1-night trip
Posted 16 hours ago
Hotel Marcel New Haven, Tapestry Collection By Hilton
Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

10/10 Excellent
"The rooms were very spacious and clean. Bedding was comfortable and the out door courtyard was lovely to relax in with a cold beverage at the end of the day."
Adam 2-night trip
Posted 22 hours ago
Hilton Garden Inn Shelton
Quality Inn

Quality Inn

10/10 Excellent
"Clean and everything was new. Bed super comfortable"
Barbara 1-night trip
Posted 2 days ago
Quality Inn
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

10/10 Excellent
"Great! Good coffee kiosk near lobby! Good cappuccino, etc."
John 4-night trip
Posted 2 days ago
Omni New Haven Hotel at Yale
Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

10/10 Excellent
"I"
Jeremie 1-night trip
Posted 3 days ago
Best Western Hartford Hotel & Suites

More cheap stays in Cheshire

Motel 6 Wethersfield, CT - Hartford

Motel 6 Wethersfield, CT - Hartford

1341 Silas Deane Hwy Wethersfield CT
$64 nightly
$74 total
Oct 6 - Oct 7
Total with taxes and fees
7/10 Good! (1,322 reviews)
Motel 6 Wethersfield, CT - Hartford
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

320 E Main St Branford CT
$65 nightly
$75 total
Oct 6 - Oct 7
Total with taxes and fees
Motel 6 New Haven - Branford, CT
Red Roof Inn Meriden

Red Roof Inn Meriden

10 Bee St Meriden CT
$87 nightly
$100 total
Oct 4 - Oct 5
Total with taxes and fees
7.6/10 Good! (1,000 reviews)
Red Roof Inn Meriden
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

120 Laning St Southington CT
$93 nightly
$107 total
Nov 1 - Nov 2
Total with taxes and fees
8.6/10 Excellent! (1,447 reviews)
Holiday Inn Express Southington by IHG
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

490 Saw Mill Rd West Haven CT
$110 nightly
$126 total
Oct 11 - Oct 12
Total with taxes and fees
Best Western Executive Hotel Of New Haven - West Haven
Hampton Inn & Suites New Haven - South - West Haven

Hampton Inn & Suites New Haven - South - West Haven

510 Saw Mill Rd West Haven CT
$127 nightly
$146 total
Oct 26 - Oct 27
Total with taxes and fees
8.4/10 Very Good! (1,003 reviews)
Hampton Inn & Suites New Haven - South - West Haven

Hotels in Cheshire with star-rating

Find out more about Cheshire

Top reasons to visit Cheshire

  • Family-Friendly Activities: Cheshire offers a variety of attractions perfect for families, including amusement parks and local parks for outdoor fun.
  • Cultural Experiences: Explore the town's quaint shops, theaters, and community events that highlight local culture.
  • Outdoor Adventures: Enjoy nature at nearby state parks, providing ample opportunities for hiking and exploration.
  • Charming Neighborhoods: Stroll through picturesque neighborhoods that showcase historical charm and friendly locals.
  • Diverse Accommodations: Find a range of lodging options, including pet-friendly and LGBTQIA-friendly accommodations for a comfortable stay.

Find great hotels near Cheshire

Cheshire, Connecticut, offers a variety of accommodation options to suit every traveler’s needs, from convenient hotels to cozy motels. Whether you're looking for a business-friendly stay or a pet-friendly retreat, you’ll find welcoming choices that prioritize comfort and service. With LGBTQIA-friendly options available, Cheshire ensures a pleasant experience for all visitors seeking a memorable getaway in this charming area.

  • Red Roof Inn Hartford - New Britain: A budget-friendly gem located 13 miles from Cheshire, the Red Roof Inn Hartford - New Britain caters to families and pet owners alike. This hotel is designed with a welcoming atmosphere and provides essential amenities for travelers with children, including free cribs and window guards for safety. With a pet-friendly policy, it welcomes dogs and cats with certain restrictions, making it an ideal choice for those traveling with furry companions. Guests appreciate the combination of affordability and family-focused services, ensuring a comfortable stay for everyone.
  • Clarion Inn North Haven - New Haven North: Situated just 8 miles from Cheshire, the Clarion Inn North Haven - New Haven North is a 3-star establishment perfect for business travelers and pet owners. This hotel combines convenience with comfort, offering various amenities tailored for professionals on the go. The pet-friendly policy allows pets with certain weight restrictions, ensuring your furry friend can join your travels. Guests have praised the hotel's commitment to providing a conducive environment for work and relaxation, making it a solid choice for those seeking both business and leisure experiences.
  • Courtyard by Marriott Waterbury Downtown: Located 7 miles from Cheshire, the Courtyard by Marriott Waterbury Downtown boasts a guest rating of 8.4 out of 10. This 3-star hotel focuses on providing an enjoyable stay with a range of dining options, including a restaurant that serves breakfast and a snack bar. Active travelers will appreciate the fitness facilities and nearby recreational activities such as hiking and skiing. With entertainment options like satellite TV and premium channels, guests can unwind after a day of exploring. The hotel's prime location near city attractions enhances its appeal for both leisure and business travelers.

Where to stay near Cheshire

Cheshire, Connecticut, offers a delightful blend of family-friendly activities, outdoor adventures, and cultural experiences. Visitors can explore its charming neighborhoods, enjoy fresh air, and partake in vibrant nightlife options. Nearby cities add to the atmosphere with friendly locals and picturesque scenery. Whether you're seeking a romantic getaway or a fun-filled family vacation, Cheshire's historical charm and welcoming vibe make it an ideal destination for all types of travelers.

  • Waterbury: Located 7 miles from Cheshire, Waterbury is a vibrant city that offers a blend of family-friendly activities and outdoor adventures. Visitors can enjoy a variety of attractions, including an amusement park and waterpark, making it an ideal spot for family outings. The city hosts events at its conference venue and features beautiful parks for outdoor enthusiasts. Peak travel months include April and the summer months, providing ample opportunities to explore the local culture and attractions.
  • Southington: Just 6 miles from Cheshire, Southington is a charming city known for its family-oriented atmosphere and adventurous spirit. The city is home to a popular amusement park and frequently hosts music concerts, ensuring there's always something happening. With peak visitor numbers in the spring and summer, Southington offers outdoor activities and opportunities for family fun, along with access to nearby waterparks and event venues that cater to a variety of interests.
  • Wallingford: Wallingford, located a mere 6 miles from Cheshire, is a city rich in culture and history, perfect for families and couples alike. Visitors can enjoy the local theater scene, explore historic college campuses, or spend a leisurely day at the golf course. The city experiences its peak travel seasons in the spring and summer, making it a perfect destination for cultural exploration, romantic getaways, and family adventures. With its charming downtown and engaging attractions, Wallingford is a must-visit.

Things to do in Cheshire

Cheshire, Connecticut, offers a delightful mix of family-friendly activities and cultural experiences. Visitors can explore quaint shops, enjoy educational outings, and catch a show at local theaters. For some fun, head to the amusement park, where excitement awaits. Don’t miss the opportunity to discover hidden treasures throughout the town, making your vacation both entertaining and enriching.

Shopping

In Cheshire, visit the Cheshire Marketplace for charming local shops and unique gifts. If you're up for a drive, check out the Westfield Meriden for a larger selection of stores and dining options, located about 15 miles away, featuring popular brands and a cozy shopping atmosphere.

Recreation

Experience tranquility at The Spa at the Farm, where you can indulge in rejuvenating treatments and unwind in serene surroundings. For outdoor fun, visit Cheshire Park for scenic walking trails and recreational activities that promote relaxation and connection with nature.

Adventure

In Cheshire, explore the scenic trails at the Cheshire Land Trust for hiking and birdwatching. Experience thrill-seeking at the nearby Lake Compounce amusement park, featuring roller coasters and water rides. Don't miss the adrenaline rush of zip-lining at the Adventure Park at Storrs, offering a unique treetop climbing experience.

Nightlife

Cheshire offers a cozy nightlife vibe with local favorites like the Cheshire Public House for craft beers and a relaxed atmosphere. For live music, check out the nearby Oakdale Theatre, where you can enjoy a variety of performances in a vibrant setting.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Cheshire

  • 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 Monday. The most expensive day to stay in Cheshire is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia's search tool to refine your preferences, such as your budget, desired location, and the type of hotel you’re looking for. To discover the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Cheshire with your flights and activities through an Expedia package deal.

Find the best attractions in and around Cheshire

Cheshire, Connecticut, is an ideal destination for family-friendly vacations, offering a rich blend of outdoor activities and cultural experiences. Visitors can explore popular attractions such as urban parks, local parks, and nearby state parks, all catering to those seeking adventure and family bonding. Whether you're looking to enjoy nature or immerse yourself in the community's culture, Cheshire has something for everyone to enjoy.

  • Roaring Brook Park: Experience the tranquility of Roaring Brook Park, nestled in Cheshire. With its eco-friendly atmosphere, this park offers family-friendly trails, picnic spots, and beautiful natural scenery, perfect for outdoor enthusiasts.
  • Lake Compounce: Located 9 miles from Cheshire, Lake Compounce is the ultimate destination for family adventure. This amusement park features thrilling rides, water attractions, and entertainment options, making it a fun-filled day for visitors of all ages.
  • Bartlem Park: Situated within Cheshire, Bartlem Park combines the charm of an urban park with family-friendly amenities. Enjoy walking trails, playgrounds, and open spaces, ideal for a relaxing day in the city while soaking up the outdoors.

Best time to go to Cheshire

The best time to visit Cheshire is dependent 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

Cheshire, Connecticut, is conveniently served by several major airports. New York's JFK Airport is 75 miles away, with nearby hotels like the 5-star Arlo Williamsburg and The William Vale, both situated 11 miles from the airport. Newark Liberty International Airport (EWR) is 87 miles from Cheshire, offering luxurious stays at The Dominick and Four Seasons Hotel New York Downtown, both 9 miles away. LaGuardia Airport (LGA) is 71 miles from Cheshire, with upscale options including The Plaza - A Fairmont Managed Hotel and The Pierre, A Taj Hotel, both about 5 miles from LGA. Transportation services are available from these hotels for easy access to the airports.

Frequently asked questions

What is the best area to stay in Cheshire?
The best area to stay in Cheshire is along Main Street, particularly near the town center, which offers convenient access to local amenities and a pleasant environment.Main Street serves as the central artery of Cheshire, featuring a mix of local businesses, dining options, and public spaces like the Cheshire Public Library and the Town Green. The architecture is primarily New England historic, creating a classic American small-town feel. This area is very walkable, making it easy to explore on foot.For couples, the area around Main Street provides a relaxed and comfortable base. You'll find a selection of local restaurants for dining out and boutique shops for browsing. The proximity to the Farmington Canal Heritage Trail offers opportunities for leisurely strolls or bike rides together.Families will also find Main Street appealing due to its central location and access to family-friendly activities. The Town Green often hosts community events, and nearby parks provide open spaces for children.
What are the best hotels in Cheshire that travelers recommend?
In Cheshire, the Cheshire Welcome Inn is a highly recommended hotel by travelers.This hotel, with an 8.4 rating, offers air-conditioned rooms and climate control for a comfortable stay. Guests appreciate its historic property design and the convenience of a yard. Free self-parking is also available. Many travelers have described the rooms as cozy and clean, the beds as comfortable, and the location as beautiful and convenient. The staff and service consistently receive great reviews. The hotel is also well-situated, being less than a mile from Bartlem Park and Lock 12 Historical Park.
What are the best family hotels in Cheshire?
For a family-friendly accommodation in Cheshire, the Cheshire Welcome Inn is an excellent option.This hotel, rated 8.4, offers cozy and clean rooms with comfortable beds, ensuring a pleasant stay for families. Guests consistently highlight the great service from the staff and the beautiful, convenient location. Families will appreciate amenities such as free WiFi and free self-parking. The hotel is also conveniently located near Bartlem Park (0.9 miles away) and Lock 12 Historical Park (0.8 miles away), offering easy access to outdoor activities. Find more child-friendly accommodations in Cheshire
What are the best budget hotels in Cheshire?
For a highly-rated budget hotel in Cheshire, the Cheshire Welcome Inn is an excellent option.The Cheshire Welcome Inn, with an 8.4 rating, offers guests a comfortable stay with complimentary WiFi and wired internet access. Travelers frequently praise the cozy and clean rooms, the comfortable beds, and the great service from the staff. Its convenient location is close to Bartlem Park, just 0.9 miles away, and Lock 12 Historical Park, 0.8 miles away, making it easy to explore local attractions. View all budget hotels in Cheshire
What are the best hotels in Cheshire near Lock 12 Historical Park?
For a hotel in Cheshire near Lock 12 Historical Park, the Cheshire Welcome Inn is a great choice.The Cheshire Welcome Inn, with an 8.4 rating, is conveniently located just 0.8 miles from Lock 12 Historical Park. Guests frequently describe the rooms as cozy and clean, with comfortable beds ensuring a pleasant stay. The hotel provides free WiFi and free self-parking, adding to its convenience. Its location is often praised as beautiful and convenient, with many guests highlighting the great service and staff.
When is the best time to go to Cheshire?
The best time to visit Cheshire is during the spring (April to June) and fall (September to October) months, when the weather is most pleasant for outdoor activities.Spring in Cheshire brings mild temperatures and blooming flora, making it ideal for exploring local parks and trails. The average temperatures range from the mid-50s to low 70s Fahrenheit, superb for a stroll through the Linear Trail or a visit to the Cheshire Hollow Farm. This period is particularly good for families looking for comfortable weather for outdoor excursions without the summer heat.Fall offers crisp air, lower humidity, and the vibrant display of New England foliage. Temperatures typically range from the 50s to 60s Fahrenheit. This season is excellent for couples who appreciate scenic drives through the countryside, apple picking at local orchards, or enjoying a cozy evening at a local restaurant after a day of exploring.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Cheshire.
How much is the nightly rate at a Cheshire hotel?
Prices for hotels in Cheshire often vary, but you can find a great deal from $74 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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