Title: Cheshire Historic District Vacation Rentals from CA $164: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6346724&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=6346724&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=6346724&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 12 - Jun 14](https://www.expedia.ca/Hotel-Search?regionId=6346724&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Cheshire Historic District vacation rentals

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/92000000/91720000/91713800/91713725/65f83363.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91720000/91713800/91713725/b3ddf07f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91720000/91713800/91713725/8e45a276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91720000/91713800/91713725/w750h486x0y3-ef058f17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

[](https://www.expedia.ca/Higganum-Hotels-Cozy-Comforts-Country-Living-At-Its-Finest-Just-10-Min-To-Downtown-Middletown.h91713725.Hotel-Information)

Haddam

10/10

Exceptional

(28 reviews)

"Fantastic experience from beginning to end! Loved every minute of my stay! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jody U.

CA $170

CA $352 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Higganum-Hotels-Cozy-Comforts-Country-Living-At-Its-Finest-Just-10-Min-To-Downtown-Middletown.h91713725.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90710000/90707200/90707157/f4556137.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90710000/90707200/90707157/28ce53e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90710000/90707200/90707157/c55a23f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/91000000/90710000/90707200/90707157/772b2c5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### #24 \*Serenity\* A Lakefront Cottage Retreat

[](https://www.expedia.ca/Middletown-Hotels-24-Serenity-A-Lakefront-Cottage-Retreat.h90707157.Hotel-Information)

Middletown

9.8/10

Exceptional

(21 reviews)

"It was our 3rd time staying and everything was as expected. New updates to the bathroom were nice surprise. Thanks again for a lovely stay while we visited our daughter at Wesleyan. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Robb F.

CA $193

CA $443 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Middletown-Hotels-24-Serenity-A-Lakefront-Cottage-Retreat.h90707157.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/2db3f072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/bdac0629.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/02f647fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/0888acaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### All New 1BR with tons of Charm

[](https://www.expedia.ca/Wallingford-Hotels-Seasons-Hospitality-Presents-All-New-1BR-With-Tons-Of-Charm.h102008958.Hotel-Information)

Wallingford Center

9.8/10

Exceptional

(8 reviews)

"Charming, unique, and very comfortable. Would surely stay again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

David S.

CA $157

CA $396 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Wallingford-Hotels-Seasons-Hospitality-Presents-All-New-1BR-With-Tons-Of-Charm.h102008958.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/126000000/125540000/125538700/125538671/95f9a3fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125540000/125538700/125538671/d3b6b0c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125540000/125538700/125538671/b438feeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125540000/125538700/125538671/f5cc3d1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### New England Tiny Home Experience: Coffee & More!

[](https://www.expedia.ca/Cromwell-Hotels-New-England-Tiny-Home-Experience-Coffee-More.h125538671.Hotel-Information)

Main Street Historic District

[](https://www.expedia.ca/Cromwell-Hotels-New-England-Tiny-Home-Experience-Coffee-More.h125538671.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/96000000/95040000/95033700/95033642/abc38fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/96000000/95040000/95033700/95033642/90f4ffc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/96000000/95040000/95033700/95033642/w905h683x59y0-78a87dbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/96000000/95040000/95033700/95033642/be573e35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Angelica’s safe haven @ west haven

[](https://www.expedia.ca/West-Haven-Hotels-Angelicas-Safe-Haven-West-Haven.h95033642.Hotel-Information)

West Haven

10/10

Exceptional

(6 reviews)

"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Veronica

CA $178

CA $450 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/West-Haven-Hotels-Angelicas-Safe-Haven-West-Haven.h95033642.Hotel-Information)

![Cookware/dishes/utensils](https://images.trvl-media.com/lodging/96000000/95040000/95032200/95032165/0eb76bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, Netflix, streaming services](https://images.trvl-media.com/lodging/96000000/95040000/95032200/95032165/446f217c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/96000000/95040000/95032200/95032165/a1d7bab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, Netflix, streaming services](https://images.trvl-media.com/lodging/96000000/95040000/95032200/95032165/f8e41211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

[](https://www.expedia.ca/New-Haven-Hotels-Urban-Oasis-3BR-Parking-Washer-Dryer-Yale-East-Rock.h95032165.Hotel-Information)

East Rock

9.8/10

Exceptional

(14 reviews)

"Thanks to the detailed information from the host check-in couldn’t have been easier. The home was clean and well-appointed. Great location with access to the Yale tram and local markets and restaurants. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Denyce D.

CA $130

CA $363 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/New-Haven-Hotels-Urban-Oasis-3BR-Parking-Washer-Dryer-Yale-East-Rock.h95032165.Hotel-Information)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107980000/107976300/107976290/da7468b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107980000/107976300/107976290/433534ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/108000000/107980000/107976300/107976290/f293483a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107980000/107976300/107976290/1bf4de91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private Apartment in Berlin

[](https://www.expedia.ca/Berlin-Hotels-Private-Apartment-In-Berlin.h107976290.Hotel-Information)

Berlin

9.2/10

Wonderful

(5 reviews)

"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Daniel L.

CA $124

CA $370 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Berlin-Hotels-Private-Apartment-In-Berlin.h107976290.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120070000/120065600/120065513/02904b89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/121000000/120070000/120065600/120065513/43b2916f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/121000000/120070000/120065600/120065513/9c9682a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/121000000/120070000/120065600/120065513/9dab6fe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### One bedroom apartment in United States of America, New Haven

[](https://www.expedia.ca/New-Haven-Hotels-One-Bedroom-Apartment-In-United-States-Of-America.h120065513.Hotel-Information)

Dwight

8.6/10

Excellent

(4 reviews)

"Apartment was very clean and well supplied, host very responsive. Location is convenient to Yale and restaurants. As noted in the listing, you'll have to carry your luggage up 4 flights of stairs. There is some street noise as is typical for that part of the city. Very happy with it overall and plan to stay again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Philip S.

CA $130

CA $280 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/New-Haven-Hotels-One-Bedroom-Apartment-In-United-States-Of-America.h120065513.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/119000000/118950000/118949700/118949631/7f5d3999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/119000000/118950000/118949700/118949631/57c8df73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118950000/118949700/118949631/8e373067.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118950000/118949700/118949631/f54053dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy East Haven Home • Near Beach & Yale

[](https://www.expedia.ca/East-Haven-Hotels-Cozy-Home-Near-New-Haven.h118949631.Hotel-Information)

Momauguin

10/10

Exceptional

(5 reviews)

"Such a cute place, loved all the nautical touches. Great space for a weekend getaway, pretty well-stocked kitchen, clean & cozy. Really appreciated the outdoor space & amenities too! And Michael the host is very responsive & helpful! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Amal A.

CA $153

CA $204 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/East-Haven-Hotels-Cozy-Home-Near-New-Haven.h118949631.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/111110000/111107100/111107034/42181017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111110000/111107100/111107034/6924fd2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111110000/111107100/111107034/7e65e0ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111110000/111107100/111107034/ffcbfb18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Family Stays: Middletown, CT

[](https://www.expedia.ca/Middletown-Hotels-Family-Stays-In-Middletown.h111107034.Hotel-Information)

Middletown

10/10

Exceptional

(21 reviews)

"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Harmony R.

CA $157

CA $306 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Middletown-Hotels-Family-Stays-In-Middletown.h111107034.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/108000000/107560000/107557500/107557460/ace6fff4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107560000/107557500/107557460/3d1f82ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107560000/107557500/107557460/d820b069.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/108000000/107560000/107557500/107557460/5a4689b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bright Downtown Studio near Yale & East Rock!

[](https://www.expedia.ca/New-Haven-Hotels-Charming-Studio-Near-Yale-Downtown-New-Haven.h107557460.Hotel-Information)

Downtown New Haven

9.0/10

Wonderful

(13 reviews)

"Everything was great and just as charming as the photo indicated. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nancy F.

CA $145

CA $332 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/New-Haven-Hotels-Charming-Studio-Near-Yale-Downtown-New-Haven.h107557460.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/120000000/119310000/119305500/119305470/faf6d210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119310000/119305500/119305470/1a3310e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119310000/119305500/119305470/96041570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119310000/119305500/119305470/eb680fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Guest Suite in Historic Home

[](https://www.expedia.ca/Middletown-Hotels-Cozy-Guest-Suite-In-Historic-Home.h119305470.Hotel-Information)

Middletown

10/10

Exceptional

(1 review)

"Perfect for a single traveler. Clean, roomy, quaint room. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brooke

CA $224

CA $321 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Middletown-Hotels-Cozy-Guest-Suite-In-Historic-Home.h119305470.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/111830000/111828700/111828646/07823851.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111830000/111828700/111828646/c873cf3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111830000/111828700/111828646/a64ee713.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/112000000/111830000/111828700/111828646/a51d4c9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy One Bedroom Apartment Centrally Located in Southbury

[](https://www.expedia.ca/Southbury-Hotels-Simple-Living-Retreat-1-Bedroom-Apartment.h111828646.Hotel-Information)

Southbury

10/10

Exceptional

(23 reviews)

"Perfect sized apartment for a short stay - very convenient to my destination"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

S

CA $119

CA $164 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Southbury-Hotels-Simple-Living-Retreat-1-Bedroom-Apartment.h111828646.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90710000/90707200/90707168/67fb0c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90710000/90707200/90707168/97101407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/91000000/90710000/90707200/90707168/c11b890f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90710000/90707200/90707168/bfd0f870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### #23 \*COMFORT & LUXURY\* 3 BR/2 BA House

[](https://www.expedia.ca/Southington-Hotels-23-COMFORT-LUXURY-3-BR2-BA-House.h90707168.Hotel-Information)

Southington

9.8/10

Exceptional

(8 reviews)

"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ryan A.

CA $217

CA $489 total

includes taxes & fees

Mar 7 - Mar 8

[](https://www.expedia.ca/Southington-Hotels-23-COMFORT-LUXURY-3-BR2-BA-House.h90707168.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122500000/122493300/122493219/a0ee27b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122500000/122493300/122493219/de0359b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/123000000/122500000/122493300/122493219/454eaea7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122500000/122493300/122493219/5cbf3c9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### One private bedroom with work space and shared home with spa.

[](https://www.expedia.ca/Rocky-Hill-Hotels-One-Private-Bedroom-With-Work-Space-And-Shared-Home-With-Spa.h122493219.Hotel-Information)

Rocky Hill

CA $141

CA $205 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Rocky-Hill-Hotels-One-Private-Bedroom-With-Work-Space-And-Shared-Home-With-Spa.h122493219.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/125000000/124360000/124360000/124359908/e5b7b978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124360000/124360000/124359908/66ba29c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124360000/124360000/124359908/ac82cf05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124360000/124360000/124359908/89f59934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Welcoming 4-bedroom house in charming Hamden

[](https://www.expedia.ca/Hamden-Hotels-Welcoming-4-Bedroom-House-In-Charming-Hamden.h124359908.Hotel-Information)

Hamden

10/10

Exceptional

(1 review)

"Host was kind and attentive. Location was convenient and the home was clean and spacious. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Renee H.

CA $312

CA $577 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Hamden-Hotels-Welcoming-4-Bedroom-House-In-Charming-Hamden.h124359908.Hotel-Information)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107010000/107006300/107006244/2e4ae9c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107010000/107006300/107006244/dc1e76d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107010000/107006300/107006244/e6288714.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107010000/107006300/107006244/0354b8c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Downtown New Haven Escape

[](https://www.expedia.ca/New-Haven-Hotels-Downtown-New-Haven-Escape.h107006244.Hotel-Information)

Dwight

8.0/10

Very good

(6 reviews)

"Great place to stay, a little tight for 2 people but good for a single. Well appointed and a great location in the city. Would definitely recommend a stay here."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael H.

CA $187

CA $343 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/New-Haven-Hotels-Downtown-New-Haven-Escape.h107006244.Hotel-Information)

![Desk, WiFi](https://images.trvl-media.com/lodging/125000000/124240000/124230500/124230490/w1416h960x24y0-3b37d4e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/125000000/124240000/124230500/124230490/cf248a51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/125000000/124240000/124230500/124230490/w1437h960x0y0-d206619d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/125000000/124240000/124230500/124230490/w1440h957x0y3-3eba8e53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### #43- Modern Luxury Log Cabin Retreat | Fire Pit

[](https://www.expedia.ca/Cheshire-Hotels-43-Modern-Luxury-Log-Cabin-Retreat-Fire-Pit.h124230490.Hotel-Information)

Prospect

CA $244

CA $578 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Cheshire-Hotels-43-Modern-Luxury-Log-Cabin-Retreat-Fire-Pit.h124230490.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/dad41f01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/4b86b544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/eacee686.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/ac508f02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### All New Studio apartment in center of town

[](https://www.expedia.ca/Wallingford-Hotels-All-New-Studio-Apartment-In-Center-Of-Town.h103029991.Hotel-Information)

Wallingford Center

10/10

Exceptional

(2 reviews)

"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nadine C.

CA $157

CA $396 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Wallingford-Hotels-All-New-Studio-Apartment-In-Center-Of-Town.h103029991.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/w1280h845x0y4-a67617b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/w1280h851x0y2-772c3b64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/w1280h848x0y2-b9f9932e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/w1280h851x0y2-c348eea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Jewel of The Cove - Historic Coastal Retreat

[](https://www.expedia.ca/East-Haven-Hotels-The-Jewel-Of-The-Cove-Historic-Coastal-Retreat.h105862474.Hotel-Information)

East Shore

9.8/10

Exceptional

(7 reviews)

"loved it so much, beautiful property 100 % would stay again "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Leilani R.

CA $282

CA $708 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/East-Haven-Hotels-The-Jewel-Of-The-Cove-Historic-Coastal-Retreat.h105862474.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-03&endDate=2026-03-04&regionId=6346724&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Cheshire+Historic+District%2C+Connecticut%2C+United+States+of+America&regionId=6346724&latLong=41.498489%2C-72.901885&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Cheshire+Historic+District%2C+Connecticut%2C+United+States+of+America&regionId=6346724&latLong=41.498489%2C-72.901885&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=APARTMENT)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Cheshire+Historic+District%2C+Connecticut%2C+United+States+of+America&regionId=6346724&latLong=41.498489%2C-72.901885&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=CONDO)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Cheshire+Historic+District%2C+Connecticut%2C+United+States+of+America&regionId=6346724&latLong=41.498489%2C-72.901885&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Cheshire+Historic+District%2C+Connecticut%2C+United+States+of+America&regionId=6346724&latLong=41.498489%2C-72.901885&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=COTTAGE)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Cheshire+Historic+District%2C+Connecticut%2C+United+States+of+America&regionId=6346724&latLong=41.498489%2C-72.901885&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=CABIN)

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## Top Cheshire Historic District Hotel Reviews

![Motel 6 New Haven - Branford, CT](https://images.trvl-media.com/lodging/1000000/60000/50400/50320/c15293e5_y.jpg)

### Motel 6 New Haven - Branford, CT

10/10 Excellent

"Good service"

[](https://expedia.ca/New-Haven-Hotels-Motel-6-New-Haven-Branford.h50320.Hotel-Information)

![Courtyard by Marriott Waterbury Downtown](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/c0e669e8_y.jpg)

### Courtyard by Marriott Waterbury Downtown

10/10 Excellent

"Clean and comfortable. Great stay. "

[](https://expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-Waterbury-Downtown.h34227.Hotel-Information)

![Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/d1cdaed7_y.jpg)

### Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection

10/10 Excellent

"Staff nice. Good environment clean and comfortable "

[](https://expedia.ca/Southbury-Hotels-Heritage-Hotel.h35389.Hotel-Information)

![Holiday Inn Express Southington by IHG](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/120068a2_y.jpg)

### Holiday Inn Express Southington by IHG

10/10 Excellent

"Great hot breakfast, quiet rooms. Overall looks nicely renovated, but there are some minor defects "

[](https://expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information)

![Home2 Suites by Hilton East Haven New Haven](https://images.trvl-media.com/lodging/1000000/10000/1500/1461/b5c018f9_y.jpg)

### Home2 Suites by Hilton East Haven New Haven

10/10 Excellent

"Clean "

[](https://expedia.ca/East-Haven-Hotels-Home2-Suites-By-Hilton-East-Haven-New-Haven.h1461.Hotel-Information)

![Courtyard by Marriott New Haven Orange-Milford](https://images.trvl-media.com/lodging/1000000/80000/79500/79426/bdad3f31_y.jpg)

### Courtyard by Marriott New Haven Orange-Milford

10/10 Excellent

"Clean room, quiet hotel"

[](https://expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-New-Haven-Orange-Milford.h79426.Hotel-Information)

![Best Western Executive Hotel Of New Haven - West Haven](https://images.trvl-media.com/lodging/1000000/30000/23300/23217/b63e42e2_y.jpg)

### Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent

"Very good, I recommend it."

[](https://expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information)

![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg)

### New Haven Hotel

10/10 Excellent

"A+ and great location."

[](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information)

![Hampton Inn & Suites Hartford/Farmington](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/393f3b68_y.jpg)

### Hampton Inn & Suites Hartford/Farmington

10/10 Excellent

"Excellent customer service "

[](https://expedia.ca/Hartford-Hotels-Hampton-Inn-And-Suites-HartfordFarmington.h2970540.Hotel-Information)

## Find out more about Cheshire Historic District

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cheshire Historic District. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Apartments in Cheshire Historic District ](https://expedia.ca/Cheshire-Historic-District-Apartments.d6346724-aaApartments.Travel-Guide-Accommodation)
- [Vacation Homes in Cheshire Historic District ](https://expedia.ca/Cheshire-Historic-District-Private-Vacation-Homes.d6346724-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Cheshire Historic District ](https://expedia.ca/Cheshire-Historic-District-Cottages.d6346724-aaCottages.Travel-Guide-Accommodation)
- [Motels in Cheshire Historic District ](https://expedia.ca/Cheshire-Historic-District-Motels.d6346724-aaMotels.Travel-Guide-Accommodation)
- [Condo Rentals in Cheshire Historic District ](https://expedia.ca/Cheshire-Historic-District-Condos.d6346724-aaCondos.Travel-Guide-Accommodation)
- [Guest Houses in Cheshire Historic District ](https://expedia.ca/Cheshire-Historic-District-Guest-Houses.d6346724-aaGuestHouses.Travel-Guide-Accommodation)
- [B&B in Cheshire Historic District ](https://expedia.ca/Cheshire-Historic-District-Bed-And-Breakfast.d6346724-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Aparthotels in Cheshire Historic District ](https://expedia.ca/Cheshire-Historic-District-Apart-Hotels.d6346724-aaApartHotels.Travel-Guide-Accommodation)
- [Farmstay in Cheshire Historic District ](https://expedia.ca/Cheshire-Historic-District-Agritourism.d6346724-aaAgritourism.Travel-Guide-Accommodation)
- [Cabin Rentals in Cheshire Historic District ](https://expedia.ca/Cheshire-Historic-District-Cabins.d6346724-aaCabins.Travel-Guide-Accommodation)
- [Villas in Cheshire Historic District ](https://expedia.ca/Cheshire-Historic-District-Villas.d6346724-aaVillas.Travel-Guide-Accommodation)
- [Inns in Cheshire Historic District ](https://expedia.ca/Cheshire-Historic-District-Inns.d6346724-aaInns.Travel-Guide-Accommodation)

## Frequently asked questions

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