Title: Cheshire Historic District Vacation Rentals from $126: Search Short-Term Rentals | Expedia.com

[Cheshire Historic District Travel Guide](https://expedia.com/Cheshire-Historic-District.dx6346724)[Hotels in Cheshire Historic District](https://expedia.com/Cheshire-Historic-District-Hotels.d6346724.Travel-Guide-Hotels)[Car Rentals in Cheshire Historic District](https://expedia.com/Car-Rentals-In-Cheshire-Historic-District.d6346724.Car-Rental-Guide)[Cheshire Historic District Vacation Packages](https://expedia.com/Cheshire-Historic-District.d6346724.Destination-Travel-Guides)

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## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=6346724&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=6346724&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=6346724&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=6346724&startDate=2026-06-19&endDate=2026-06-21&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

![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)

![Hair dryer](https://images.trvl-media.com/lodging/121000000/120070000/120065600/120065513/a94b7e4c.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)

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

[](https://www.expedia.com/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.

$180 nightly

$204 total

Mar 2 - Mar 3

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/108000000/107980000/107976300/107976290/1bf4de91.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)

### Private Apartment in Berlin

[](https://www.expedia.com/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.

$224 nightly

$254 total

Mar 8 - Mar 9

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/113000000/113000000/112999100/112999076/9fd3ea2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/113000000/112999100/112999076/d0920f95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/113000000/112999100/112999076/c48a29ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/113000000/112999100/112999076/w4027h3019x0y0-7deed843.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

###  The Nest At Elm City Flats.

[](https://www.expedia.com/New-Haven-Hotels-Overlook-New-Haven-In-This-2-BDR-Peaceful-Carribean-Nest.h112999076.Hotel-Information)

West New Haven

9.6/10

Exceptional

(9 reviews)

"We had a great stay at this apartment. You do have to go up three flight of stairs but thankfully we were able to climb them. "

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

Joan S.

$204 nightly

$232 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/New-Haven-Hotels-Overlook-New-Haven-In-This-2-BDR-Peaceful-Carribean-Nest.h112999076.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/127000000/126270000/126261000/126260944/d03367e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/127000000/126270000/126261000/126260944/w1176h857x1y0-d34d8f0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, WiFi](https://images.trvl-media.com/lodging/127000000/126270000/126261000/126260944/w1175h1559x0y0-31970a51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126270000/126261000/126260944/w1176h865x1y0-43e0b4e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Room in charming New Haven near Yale/Hospitals!

[](https://www.expedia.com/New-Haven-Hotels-Cozy-Room-In-Charming-New-Haven-Near-YaleHospitals.h126260944.Hotel-Information)

The Hill

$137 nightly

$155 total

Feb 28 - Mar 1

Total with taxes and fees

[](https://www.expedia.com/New-Haven-Hotels-Cozy-Room-In-Charming-New-Haven-Near-YaleHospitals.h126260944.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99480000/99476700/99476616/7ce55fe4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/100000000/99480000/99476700/99476616/897c3b48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99480000/99476700/99476616/b3af2d99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/100000000/99480000/99476700/99476616/519bb10d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### #26 Beautifully Renovated 2 BR Home

[](https://www.expedia.com/Plainville-Hotels-26-Beautifully-Renovated-2-BR-Home.h99476616.Hotel-Information)

Plainville

10/10

Exceptional

(4 reviews)

"We thoroughly enjoyed our stay! The space was great for our family of 4\. Would recommend!"

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

LaTanya W.

[](https://www.expedia.com/Plainville-Hotels-26-Beautifully-Renovated-2-BR-Home.h99476616.Hotel-Information)

![Desk, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111780000/111775100/111775014/1017778e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111780000/111775100/111775014/bd339fc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/112000000/111780000/111775100/111775014/w1350h899x0y0-2d8856e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111780000/111775100/111775014/1bdf8a9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Yale Casa Verde Studio

[](https://www.expedia.com/New-Haven-Hotels-Yale-Casa-Verde-Studio.h111775014.Hotel-Information)

Dwight

9.6/10

Exceptional

(9 reviews)

"Had a great stay!"

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

Jeffrey C.

$181 nightly

$205 total

Feb 28 - Mar 1

Total with taxes and fees

[](https://www.expedia.com/New-Haven-Hotels-Yale-Casa-Verde-Studio.h111775014.Hotel-Information)

![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)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/92000000/91720000/91713800/91713725/034a5b48.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)

![Exterior](https://images.trvl-media.com/lodging/92000000/91720000/91713800/91713725/b3ddf07f.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.com/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.

$226 nightly

$256 total

Mar 8 - Mar 9

Total with taxes and fees

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

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

![Property grounds](https://images.trvl-media.com/lodging/123000000/122500000/122493300/122493219/b781e6ae.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)

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

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

Rocky Hill

$134 nightly

$151 total

Feb 28 - Mar 1

Total with taxes and fees

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/125000000/124550000/124548600/124548580/f69faf0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels](https://images.trvl-media.com/lodging/125000000/124550000/124548600/124548580/2806dfd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124550000/124548600/124548580/e3f04cda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/125000000/124550000/124548600/124548580/511a30dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2BR Apartment Near Wesleyan 301

[](https://www.expedia.com/Middletown-Hotels-Apartment-In-Middletown-Wesleyan-301.h124548580.Hotel-Information)

Washington Street Historic District

$240 nightly

$272 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Middletown-Hotels-Apartment-In-Middletown-Wesleyan-301.h124548580.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/123000000/122140000/122137200/122137179/85c49a6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122140000/122137200/122137179/00e5ce8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122140000/122137200/122137179/9533b0e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/123000000/122140000/122137200/122137179/b9d9b74e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2BR Apartment Near Wesleyan 102

[](https://www.expedia.com/Middletown-Hotels-Apartment-In-Middletown-Wesleyan102.h122137179.Hotel-Information)

Washington Street Historic District

$224 nightly

$253 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Middletown-Hotels-Apartment-In-Middletown-Wesleyan102.h122137179.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/99000000/98260000/98257500/98257429/97ba6294.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/99000000/98260000/98257500/98257429/4686f259.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/99000000/98260000/98257500/98257429/e70265ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/99000000/98260000/98257500/98257429/bb6c9c37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Yale Casa Azul Studio

[](https://www.expedia.com/New-Haven-Hotels-Yale-Casa-Azul-Studio.h98257429.Hotel-Information)

Dwight

6.4/10

(5 reviews)

"It was really nice place, people were so nice, good area"

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

Sophia T.

$165 nightly

$187 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/New-Haven-Hotels-Yale-Casa-Azul-Studio.h98257429.Hotel-Information)

![Apartment (1 Bedroom) | Private kitchen | Fridge, coffee/tea maker](https://images.trvl-media.com/lodging/126000000/125160000/125152000/125151932/a618c812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/126000000/125160000/125152000/125151932/fcd1b186.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/126000000/125160000/125152000/125151932/bddafb8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, individually decorated, individually furnished](https://images.trvl-media.com/lodging/126000000/125160000/125152000/125151932/e49e9e7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Landing Furnished Apartment Near Yale University

[](https://www.expedia.com/New-Haven-Hotels-Landing-Chic-1bd.h125151932.Hotel-Information)

Downtown New Haven

[](https://www.expedia.com/New-Haven-Hotels-Landing-Chic-1bd.h125151932.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/f8e41211.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)

![Hair dryer](https://images.trvl-media.com/lodging/96000000/95040000/95032200/95032165/d9bfd1d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/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.

$254 nightly

$264 total

Mar 1 - Mar 2

Total with taxes and fees

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

![Living area](https://images.trvl-media.com/lodging/112000000/111820000/111815700/111815688/6facc203.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111820000/111815700/111815688/61794cd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/112000000/111820000/111815700/111815688/cb885f74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111820000/111815700/111815688/231963b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wooster Gem - Walk to Pizza & Yale! - FREE Parking and Laundry

[](https://www.expedia.com/New-Haven-Hotels-Stylish-2-Bedroom-Apartment-In-Lovely-Wooster-Square-New-Haven-Near-Yale.h111815688.Hotel-Information)

Mill River

10/10

Exceptional

(1 review)

"The host was very responsive. I would recommend Vrbo as well as this host for future stays."

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

Larmeka A.

$298 nightly

$337 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/New-Haven-Hotels-Stylish-2-Bedroom-Apartment-In-Lovely-Wooster-Square-New-Haven-Near-Yale.h111815688.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/112000000/111830000/111824500/111824460/62b2e5a8_edited_33e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111830000/111824500/111824460/efeecab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111830000/111824500/111824460/624102e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111830000/111824500/111824460/a5ee2415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

[](https://www.expedia.com/Cheshire-Hotels-Quiet-2-Bedroom-Apartment-In-Wonderful-Cheshire-With-WiFi-And-Beautiful-Views.h111824460.Hotel-Information)

Cheshire

9.4/10

Exceptional

(16 reviews)

"Great Location - all the amenities you need for a nice restful stay. Did not have to reach-out to the host at all during our stay. "

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

Robert S.

$149 nightly

$168 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Cheshire-Hotels-Quiet-2-Bedroom-Apartment-In-Wonderful-Cheshire-With-WiFi-And-Beautiful-Views.h111824460.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/101000000/100400000/100397900/100397846/453bb440.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100400000/100397900/100397846/b44a1a8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100400000/100397900/100397846/86a2247f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/101000000/100400000/100397900/100397846/4b94d1f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### #31 - Downtown Terryville- 1 Br

[](https://www.expedia.com/Terryville-Hotels-31-Downtown-Terryville-1-Br.h100397846.Hotel-Information)

Plymouth

10/10

Exceptional

(1 review)

"In convenient safe area. Os is easy to contact"

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

Gina P.

[](https://www.expedia.com/Terryville-Hotels-31-Downtown-Terryville-1-Br.h100397846.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/104000000/103790000/103788100/103788056/5b4a24dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/104000000/103790000/103788100/103788056/f9827073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103790000/103788100/103788056/w1018h683x3y0-a5aee002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/104000000/103790000/103788100/103788056/b011751f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Sicilian

[](https://www.expedia.com/New-Haven-Hotels-The-Sicilian.h103788056.Hotel-Information)

West New Haven

9.4/10

Exceptional

(13 reviews)

"Perfect spot for a quick overnight. Cozy and very nicely decorated. "

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

Jason S.

$212 nightly

$240 total

Feb 28 - Mar 1

Total with taxes and fees

[](https://www.expedia.com/New-Haven-Hotels-The-Sicilian.h103788056.Hotel-Information)

![Bar (on property)](https://images.trvl-media.com/lodging/108000000/107010000/107006300/107006237/5f9ccc1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107010000/107006300/107006237/f83357c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/108000000/107010000/107006300/107006237/a03ed17d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107010000/107006300/107006237/a5ed0b35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Studio Stay On Howe

[](https://www.expedia.com/New-Haven-Hotels-Cozy-Studio-Near-ArchitectureDrama-Schools-Yale.h107006237.Hotel-Information)

Dwight

9.0/10

Wonderful

(4 reviews)

"Cute, clean property good for a visit to New Haven for a single or couple. The area is a little noisy, but that's the price you pay for being in close walking distance to everything you'd want to be in close walking distance to! Would definitely stay again. "

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

Robin A.

$267 nightly

$274 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/New-Haven-Hotels-Cozy-Studio-Near-ArchitectureDrama-Schools-Yale.h107006237.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)

![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)

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

### Downtown New Haven Escape

[](https://www.expedia.com/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.

$233 nightly

$241 total

Feb 28 - Mar 1

Total with taxes and fees

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122400000/122391400/122391367/2372fa1d.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/123000000/122400000/122391400/122391367/0984b254.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122400000/122391400/122391367/a0cac3d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122400000/122391400/122391367/659e94b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Southington-Hotels-Welcoming-1500-Square-Foot-3-Bedroom-House-Completely-Remodeled-In-Southington.h122391367.Hotel-Information)

Southington

10/10

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

Cindy M.

$539 nightly

$611 total

Mar 7 - Mar 8

Total with taxes and fees

[](https://www.expedia.com/Southington-Hotels-Welcoming-1500-Square-Foot-3-Bedroom-House-Completely-Remodeled-In-Southington.h122391367.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.com/Hotel-Search?startDate=2026-03-13&endDate=2026-03-14&regionId=6346724&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

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## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Cheshire+Historic+District%2C+Connecticut%2C+United+States+of+America&regionId=6346724&latLong=41.498489%2C-72.901885&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Cheshire+Historic+District%2C+Connecticut%2C+United+States+of+America&regionId=6346724&latLong=41.498489%2C-72.901885&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=APARTMENT)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Cheshire+Historic+District%2C+Connecticut%2C+United+States+of+America&regionId=6346724&latLong=41.498489%2C-72.901885&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=CONDO)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Cheshire+Historic+District%2C+Connecticut%2C+United+States+of+America&regionId=6346724&latLong=41.498489%2C-72.901885&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Cheshire+Historic+District%2C+Connecticut%2C+United+States+of+America&regionId=6346724&latLong=41.498489%2C-72.901885&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=COTTAGE)

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Cheshire+Historic+District%2C+Connecticut%2C+United+States+of+America&regionId=6346724&latLong=41.498489%2C-72.901885&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=CABIN)

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## Top Cheshire Historic District Hotel Reviews

![Extended Stay America Suites Hartford Farmington](https://images.trvl-media.com/lodging/1000000/160000/151100/151013/02939ae3_y.jpg)

### Extended Stay America Suites Hartford Farmington

10/10 Excellent

"Clean"

[](https://expedia.com/Hartford-Hotels-Extended-Stay-America-Suites-Hartford-Farmington.h151013.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

"perfect room and ammenities. great place to stay. "

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

![Holiday Inn Cheshire - Southington by IHG](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/a3c0d287_y.jpg)

### Holiday Inn Cheshire - Southington by IHG

10/10 Excellent

"Yes"

[](https://expedia.com/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.Hotel-Information)

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

### New Haven Hotel

10/10 Excellent

"The room was great, I love that it had a separate sink outside of the bathroom. Beds were comfortable and linens cozy."

[](https://expedia.com/New-Haven-Hotels-New-Haven-Hotel.h36721.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 room, staff was great, amenities, walking distance to all amazing restaurants, safe and quite "

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

![Omni New Haven Hotel at Yale](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/7466af25_y.jpg)

### Omni New Haven Hotel at Yale

10/10 Excellent

"Comfortable, clean, quiet. Perfect atay"

[](https://expedia.com/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.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

"Everything was amazing great stay !! "

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

![Comfort Inn Wethersfield - Hartford](https://images.trvl-media.com/lodging/1000000/20000/17700/17635/13705d6b_y.jpg)

### Comfort Inn Wethersfield - Hartford

8/10 Good

"Clean room "

[](https://expedia.com/Hartford-Hotels-Comfort-Inn-Wethersfield-Hartford.h17635.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

"Clean, safe, great place to stay"

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

## Find out more about Cheshire Historic District

**Everything you need to know about Cheshire Historic District vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cheshire Historic District vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cheshire Historic District vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Cheshire Historic District vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Cheshire Historic District. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cheshire Historic District in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $126 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Cheshire Historic District rentals**

At Expedia, we put the best Cheshire Historic District vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cheshire Historic District rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cheshire Historic District vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cheshire Historic District. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

- Trending destinations on Expedia.com
- All accommodation types in Cheshire Historic District

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- [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals)
- [Palm Springs Vacation Rentals ](https://www.expedia.com/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals)
- [Florida Keys Vacation Rentals ](https://www.expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)
- [Lake Tahoe Vacation Rentals ](https://www.expedia.com/South-Lake-Tahoe-Vacation-Rentals.d10150.Travel-Guide-VacationRentals)
- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

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

## Frequently asked questions

### Can I find vacation rentals in Cheshire Historic District?

### What are some of the best vacation home rentals in Cheshire Historic District?

### What can I see and do in Cheshire Historic District?

### What are vacation rentals like in Cheshire Historic District?

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