Holiday Homes in Cheshire Historic District

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Cheshire Historic District holiday homes

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is €256
includes taxes & fees
3 Jun - 4 Jun
Once the old Schools house now a newly furnished Apartment

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"The house was cozy and comfortable. The location was great while dropping our son off at Wesleyan University for his sophomore year. The lake was a peaceful place to relax and read."
United States
julia h.
The price is €328
includes taxes & fees
16 Jun - 17 Jun
#24 *Serenity* A Lakefront Cottage Retreat

1 Min to I-91 - Newly Renovated Modern 2 BR Home

1 Min to I-91 - Newly Renovated Modern 2 BR Home
Berlin
The price is €270
includes taxes & fees
22 Jun - 23 Jun
1 Min to I-91 - Newly Renovated Modern 2 BR Home

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Fair Haven
9.6 out of 10, Exceptional, (15 reviews)
"A cozy pet and family-friendly property. Very spacious."
United States
Wallace R.
The price is €284
includes taxes & fees
3 Jun - 4 Jun
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Southington
9.0 out of 10, Wonderful, (7 reviews)
"We enjoyed our stay! And happy with most!!!!"
United States
Dawn H.
The price is €455
includes taxes & fees
3 Jun - 4 Jun
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT

Quiet Comfort Meets Coastal Charm: A Perfect Family Retreat in East Haven

Quiet Comfort Meets Coastal Charm: A Perfect Family Retreat in East Haven
Foxon
The price is €262
includes taxes & fees
15 Jun - 16 Jun
Quiet Comfort Meets Coastal Charm: A Perfect Family Retreat in East Haven

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Waterbury
8.0 out of 10, Very good, (1 review)
"I had an emergency and was only able to stay one night, but enjoyed my stay "
United States
Dirk N.
The price is €130
includes taxes & fees
3 Jun - 4 Jun
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

McAngel Haven: 5 mins from Yale

McAngel Haven: 5 mins from Yale
West Haven
9.6 out of 10, Exceptional, (21 reviews)
"Excellent location Clean and spacious Comfortable beds "
United States
Joseph T.
The price is €450
includes taxes & fees
8 Jun - 9 Jun
McAngel Haven: 5 mins from Yale

The Jewel of The Cove - Historic Coastal Retreat

The Jewel of The Cove - Historic Coastal Retreat
East Shore
9.8 out of 10, Exceptional, (9 reviews)
"This was a great place to stay in New Haven, and a lot of care has gone into making it a welcoming house."
United States
Geoffrey H.
The price is €468
includes taxes & fees
9 Jun - 10 Jun
The Jewel of The Cove - Historic Coastal Retreat

#26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home
Plainville
10.0 out of 10, Exceptional, (5 reviews)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
The price is €279
includes taxes & fees
18 Jun - 19 Jun
#26 Beautifully Renovated 2 BR Home

#27- Luxury Collection

#27- Luxury Collection
Southington
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home, well designed and spacious rooms. Host was fantastic and communication was great! Thank you"
United States
C B.
The price is €394
includes taxes & fees
8 Jun - 9 Jun
#27- Luxury Collection

#28- *Modern Bungalow*

#28- *Modern Bungalow*
New Britain
8.8 out of 10, Excellent, (3 reviews)
"This stay was very comfortable and also not too fat from the Convention Center either "
United States
Vicente B.
#28- *Modern Bungalow*

Welcoming 4-bedroom house in charming Hamden

Welcoming 4-bedroom house in charming Hamden
Hamden
10.0 out of 10, Exceptional, (2 reviews)
"Host was kind and attentive. Location was convenient and the home was clean and spacious. "
United States
Renee H.
The price is €448
includes taxes & fees
3 Jun - 4 Jun
Welcoming 4-bedroom house in charming Hamden

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Shelton
The price is €421
includes taxes & fees
4 Jun - 5 Jun
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

#29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.4 out of 10, Exceptional, (6 reviews)
"Great place! "
United States
Gail R.
The price is €399
includes taxes & fees
10 Jun - 11 Jun
#29 - Modern 5 Bedroom/2 Bath

Coastal Landing Stay

Coastal Landing Stay
East Shore
The price is €474
includes taxes & fees
10 Jun - 11 Jun
Coastal Landing Stay

Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches
East Shore
8.8 out of 10, Excellent, (3 reviews)
"Fantastic place, amazing hosts, 100% recommend! "
United States
Zach P.
The price is €741
includes taxes & fees
9 Jun - 10 Jun
Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Watertown
10.0 out of 10, Exceptional, (3 reviews)
"Everything was good just needed to have a tV in each room trash cans also"
United States
Deborah B.
The price is €454
includes taxes & fees
8 Jun - 9 Jun
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

1-bedroom vacation home 22 minutes from Quinnipiac University

1-bedroom vacation home 22 minutes from Quinnipiac University
Wolcott
9.6 out of 10, Exceptional, (4 reviews)
"Very clean and the host was great "
United States
David G.
1-bedroom vacation home 22 minutes from Quinnipiac University

#30 - Spacious & Cozy!

#30 - Spacious & Cozy!
Southington
6.8 out of 10, (5 reviews)
"the house was great for our needs - it was nicely furnished fully stocked with the essentials in the kitchen. the host checked in when it was especially cold to ensure the heat and water were working correctly. the living room was very comfortable with leather reclining chairs and a gas fireplace that heated the room very well. We enjoyed how easy our stay was and recommend this location "
United States
Kaity B.
The price is €381
includes taxes & fees
3 Jun - 4 Jun
#30 - Spacious & Cozy!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cheshire Historic District Hotel Reviews

Find out more about Cheshire Historic District

Cheshire Historic District Holiday Homes information

Number of reviews
11,281
Accommodation
221 Holiday Homes
Lowest Price
€58
Highest Price
€149

Explore a world of travel with Expedia