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Holiday Homes in Cheshire Historic District

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Cheshire Historic District holiday homes

A modern living room with a sofa, coffee table, and a TV mounted on the wall.

1. 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, (16 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is €269
includes taxes & fees
12 Nov - 13 Nov
Once the old Schools house now a newly furnished Apartment
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

2. Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (3 reviews)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
The price is €479
includes taxes & fees
8 Nov - 9 Nov
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
A staircase with a handrail, a potted plant with yellow flowers, and a sign above the stairs.

3. 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 €127
includes taxes & fees
14 Nov - 15 Nov
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A two-story house with a porch, a front door with a wreath, and a small garden area.

4. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (12 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is €289
includes taxes & fees
1 Nov - 2 Nov
Bear Retreat - 2-bedroom house in Waterbury
A modern kitchen with stainless steel appliances, a central island, and a built-in oven.

5. #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.
#27- Luxury Collection
A room with a fireplace, two sofas, a rug, and a robotic vacuum cleaner.

6. The Cottage by the Woods -private getaway to relax

The Cottage by the Woods -private getaway to relax
Meriden
The Cottage by the Woods -private getaway to relax
Veterans Park, near the house

7. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (34 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
Family Stays: Middletown, CT
A spacious living room with large windows, a fireplace, and a view of the outdoors.

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

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Watertown
9.0 out of 10, Wonderful, (6 reviews)
"In town to visit our new grandchild. It was just my husband and me. It had more then enough room and was very comfortable."
United States
Elizabeth H.
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A marina with multiple docks and boats, surrounded by residential buildings and greenery.

9. Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Fair Haven
8.0 out of 10, Very good, (6 reviews)
"Thanks for hosting us! It was clean and nice. For future guests, a long body mirror might be nice but we had a wonderful time and appreciated you bringing us extra towels quickly!"
United States
Jamie S.
The price is €190
includes taxes & fees
2 Nov - 3 Nov
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
A living room with a sofa, a coffee table, a TV, and a lamp.

10. Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale

Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale
Newhallville
The price is €358
includes taxes & fees
1 Nov - 2 Nov
Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale
A hot tub in a covered outdoor area with a view of trees and a fence.

11. Lakehaven • Hot Tub, Decks, Fires & More

Lakehaven • Hot Tub, Decks, Fires & More
Plymouth
10.0 out of 10, Exceptional, (1 review)
"Great find!! Amazing views, house was superb!"
United States
Iva B.
Lakehaven • Hot Tub, Decks, Fires & More
A marina with multiple docks and boats, surrounded by residential buildings and greenery.

12. Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Fair Haven
9.8 out of 10, Exceptional, (16 reviews)
"A cozy pet and family-friendly property. Very spacious."
United States
Wallace R.
The price is €265
includes taxes & fees
2 Nov - 3 Nov
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
A modern living room with a grey sofa, a dining table, and a kitchen in the background.

13. #22- 4 Br 2 Ba house-Central CT

#22- 4 Br 2 Ba house-Central CT
New Britain
9.0 out of 10, Wonderful, (2 reviews)
"Host was great and responsive and the property was perfect for what we needed."
United States
Hilda C.
The price is €401
includes taxes & fees
7 Nov - 8 Nov
#22- 4 Br 2 Ba house-Central CT
A living room with a dark grey sofa, a wooden coffee table with a vase of white flowers, a patterned rug, and a ceiling fan.

14. Cozy East Haven Home • Near Beach & Yale

Cozy East Haven Home • Near Beach & Yale
Momauguin
10.0 out of 10, Exceptional, (12 reviews)
"Property was clean and had all amenities we needed. Easy check in and check out"
United States
Sarah S.
The price is €159
includes taxes & fees
9 Nov - 10 Nov
Cozy East Haven Home • Near Beach & Yale
A modern living room with a leather sofa, a dining table with chairs, a kitchen area with white cabinets, and a chandelier.

15. #29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.0 out of 10, Wonderful, (7 reviews)
"Great place! "
United States
Gail R.
#29 - Modern 5 Bedroom/2 Bath
A living room with a staircase, a sofa, a coffee table, and a TV.

16. Loft •Pool • Gym • Free Parking • Near Yale

Loft •Pool • Gym • Free Parking • Near Yale
Orange
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed our stay. Host was accommodating and quick to respond when we encountered issues."
United States
Ali B.
The price is €253
includes taxes & fees
1 Nov - 2 Nov
Loft •Pool • Gym • Free Parking • Near Yale
A modern living room with hardwood flooring, a leather sofa, a round coffee table, and a wooden side table. There is a dining area with a table and chairs visible in the background.

17. 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 €384
includes taxes & fees
2 Nov - 3 Nov
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
A covered porch with a wicker chair and a potted plant.

18. 3-bedroom house just walking distance from Yale and Downtown

3-bedroom house just walking distance from Yale and Downtown
Dixwell
10.0 out of 10, Exceptional, (7 reviews)
"Great stay!"
United States
Mark S.
The price is €347
includes taxes & fees
2 Nov - 3 Nov
3-bedroom house just walking distance from Yale and Downtown
A marina with multiple docks and boats, surrounded by a forested area and residential buildings.

19. Gorgeous Waterfront 2:1 - 2 houses in 1 building.

Gorgeous Waterfront 2:1 - 2 houses in 1 building.
Fair Haven
The price is €646
includes taxes & fees
2 Nov - 3 Nov
Gorgeous Waterfront 2:1 - 2 houses in 1 building.
Lovely spacious kitchen to cook and enjoy your meals; Large island to sit and eat.

20. Heavenly Home in New Haven /5 mins drive from Yale

Heavenly Home in New Haven /5 mins drive from Yale
Fair Haven
9.2 out of 10, Wonderful, (24 reviews)
"Place was so cute and spacious. Owner was awesome too! Definitely recommend."
United States
Aliza T.
The price is €693
includes taxes & fees
8 Nov - 9 Nov
Heavenly Home in New Haven /5 mins drive from Yale
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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Top Cheshire Historic District Hotel Reviews

Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

10/10 Excellent
"Everything was great! Would recommend this Hotel to family."
Starr 2-night trip
Posted 7 hours ago
Courtyard by Marriott Waterbury Downtown

Find out more about Cheshire Historic District

Cheshire Historic District Holiday Homes information

Number of reviews
140
Accommodation
228 Holiday Homes
Lowest Price
€127
Highest Price
€693

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