Cheshire Holiday Rentals, Connecticut: Private House Rentals

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

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Go beyond your typical stay in Cheshire

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Our top choices for Cheshire hotels

Standard Room, 2 Double Beds | Blackout curtains, iron/ironing board, free WiFi, alarm clocks

1. Cheshire Welcome Inn

Cheshire

Stacey

2.140.237 ₫

2.461.272 ₫ total

includes taxes & fees

26 Aug - 27 Aug

Premium bedding, desk, laptop workspace, iron/ironing board

2. Holiday Inn Cheshire - Southington by IHG

Southington

Robert

3.159.310 ₫

3.633.207 ₫ total

includes taxes & fees

6 Sept - 7 Sept

Room, 2 Queen Beds, Non Smoking | Pillow-top beds, desk, blackout curtains, iron/ironing board

3. Days Inn by Wyndham Southington

Southington

Lindsey

2.323.790 ₫

2.672.358 ₫ total

includes taxes & fees

17 Aug - 18 Aug

In-room safe, desk, laptop workspace, blackout curtains

4. Courtyard by Marriott Waterbury Downtown

Waterbury

Elizabeth

1.975.221 ₫

2.271.504 ₫ total

includes taxes & fees

6 Sept - 7 Sept

5. Fairfield by Marriott Inn & Suites Wallingford New Haven

Wallingford

Thierry

3.266.361 ₫

3.756.315 ₫ total

includes taxes & fees

6 Sept - 7 Sept

Standard Room, 2 Queen Beds | Desk, iron/ironing board, free WiFi, alarm clocks

Desk, iron/ironing board, free WiFi, alarm clocks

6. Quality Inn Waterbury East

Waterbury

Chelsea

2.419.092 ₫

2.781.956 ₫ total

includes taxes & fees

26 Aug - 27 Aug

Suite, 1 King Bed with Sofa bed, Non Smoking | In-room safe, desk, blackout curtains, iron/ironing board

7. Comfort Inn & Suites Meriden East

Meriden

Sharmarie

2.345.984 ₫

2.697.882 ₫ total

includes taxes & fees

2 Sept - 3 Sept

37-inch flat-screen TV with cable channels, TV

8. Homewood Suites by Hilton Wallingford-Meriden

Wallingford

Timothy

3.750.702 ₫

4.313.307 ₫ total

includes taxes & fees

7 Sept - 8 Sept

Suite, 1 King Bed, Non Smoking, Refrigerator & Microwave | Desk, blackout curtains, iron/ironing board, free cots/infant beds

9. Best Western Plus New England Inn & Suites

Berlin

Taneesha

2.734.239 ₫

3.144.375 ₫ total

includes taxes & fees

19 Aug - 20 Aug

10. Courtyard New Haven Wallingford

Wallingford

Marjory

3.861.669 ₫

4.440.919 ₫ total

includes taxes & fees

23 Aug - 24 Aug

Premium bedding, pillow-top beds, in-room safe, desk

11. Residence Inn by Marriott Southington

Southington

Julie-Ann

3.894.264 ₫

4.478.404 ₫ total

includes taxes & fees

16 Aug - 17 Aug

Studio, 2 Double Beds, Non Smoking | Desk, blackout curtains, iron/ironing board, free WiFi

Studio, 1 Queen Bed, Accessible, Non Smoking | Private kitchen | Coffee/tea maker, full-sized fridge, microwave, stovetop

12. Extended Stay America Suites Hartford Meriden

Meriden

Hadiyah

2.587.203 ₫

2.975.323 ₫ total

includes taxes & fees

16 Aug - 17 Aug

Premium bedding, down duvets, pillow-top beds, desk

13. Holiday Inn Express Southington by IHG

Southington

Rodwell

2.399.285 ₫

2.759.178 ₫ total

includes taxes & fees

16 Aug - 17 Aug

14. Red Roof Inn Meriden

Meriden

David

2.069.971 ₫

2.380.467 ₫ total

includes taxes & fees

30 Aug - 31 Aug

15. Cambria Hotel New Haven University Area

West River

Vincent

3.401.078 ₫

3.911.240 ₫ total

includes taxes & fees

16 Aug - 17 Aug

Studio, 1 King Bed with Sofa bed | Private kitchen | Coffee/tea maker

16. Residence Inn by Marriott New Haven Hamden

Hamden

Constance

4.647.580 ₫

5.344.717 ₫ total

includes taxes & fees

23 Aug - 24 Aug

17. Clarion Inn North Haven - New Haven North

North Haven

Katie

2.795.337 ₫

3.214.637 ₫ total

includes taxes & fees

13 Sept - 14 Sept

18. Homewood Suites by Hilton Southington, CT

Southington

Stephenie

3.618.324 ₫

4.161.073 ₫ total

includes taxes & fees

6 Sept - 7 Sept

Suite, 1 King Bed | Living area | 42-inch LCD TV with satellite channels, TV

19. Hilton Garden Inn Wallingford/Meriden

Wallingford

Brian

3.621.927 ₫

4.165.216 ₫ total

includes taxes & fees

7 Sept - 8 Sept

In-room safe, iron/ironing board, free cots/infant beds

20. Hampton Inn Waterbury

Waterbury

Millard

3.087.968 ₫

3.551.163 ₫ total

includes taxes & fees

8 Sept - 9 Sept

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Stay near popular Cheshire attractions

Roaring Brook Park

8.4/10 (12 reviews)

Connecticut's tallest single-drop waterfall cascades dramatically 80 feet through lush woodland. Hike the moderate one-mile loop trail in spring for the most impressive water flow after seasonal rains.

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Barker Character, Comic and Cartoon Museum

7.0/10 (12 reviews)

Step back in time at this treasure trove of over 80,000 character toys and memorabilia from 1873 to today. Explore meticulously arranged exhibits that evoke nostalgia across generations of American pop culture.

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Cheshire Hollow Farm

8.4/10 (15 reviews)

This 94-acre working farm invites visitors to interact with pygmy goats, miniature horses, and other friendly animals. Experience nature hikes, scavenger hunts, and seasonal activities like pumpkin picking and hayrides.

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Maplecroft Plaza Shopping Center

8.6/10 (14 reviews)

Maplecroft Plaza serves local Cheshire residents with essential retail shops in a convenient setting. Browse the diverse stores during weekday mornings when the atmosphere is most relaxed and parking is plentiful.

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Lock 12 Historical Park

Discover America's canal history at Lock 12 Historical Park, home to the only intact lock from the 1828 Farmington Canal. Walk the heritage trail after exploring the lock-keeper's house and canal artefacts.

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Bartlem Park

8.6/10 (13 reviews)

This vibrant community hub offers sports fields, a playground, and the Cheshire Community Pool for active pursuits. Enjoy a family picnic in the pavilion area or time your visit for the annual Autumn Festival in September.

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Drazen Orchards

7.8/10 (10 reviews)

This family-owned orchard invites you to pick seasonal fruits straight from the trees since 1951. Savour the harvest experience with weekend wagon rides and farm-fresh treats at their charming stand.

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Quinnipiac Recreation Area

8.6/10 (14 reviews)

This 59-acre community park offers well-maintained fields for football, lacrosse, and in-line skating. Families can enjoy the pavilion's picnic areas while watching local sports events unfold.

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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.

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Top Cheshire Hotel Reviews

Motel 6 New Haven - Branford, CT

10/10 Excellent

"Excellent service great staff"

New Haven Hotel

10/10 Excellent

"Modern, nice looking hotel. Very clean for the most part. Didn’t like that our bathtub had a slip proof mat that had rust color streaks all across it. Only real complaint, oh and the their coffee maker wasn’t working. Our room was also located near the ice machine and we could hear the ice being dropped regularly. That was pretty annoying once we got in bed. I would stay here again though, just don’t want a room near ice machine."

Courtyard by Marriott New Haven Orange-Milford

10/10 Excellent

"Excellent, simple, dining facilities that gave us an opportunity to have a small but good dinner and an interesting breakfast without relieving the facility. It was a bit of aExcellent, simple, dining facilities that gave us an opportunity to have a small but good dinner and an interesting breakfast without relieving the facility. It was a bit of a surprise surprise"

Best Western Hartford Hotel & Suites

10/10 Excellent

"Was very nice, the staff is fine."

Hilton Garden Inn Milford

10/10 Excellent

"Loved the pool!"

Motel 6 Wethersfield, CT - Hartford

10/10 Excellent

"It was easy and convenient, we were traveling late and it was open. The beds are a okay, need better sheets and pillows. But the bed was not hard. It was quiet and convenient location."

The Capitol Hotel

8/10 Good

"An Honest Review from Someone Who Travels for Work I read the previous reviews before my stay, and honestly, I was a little terrified when my assistant booked this property for my 4-day work trip. After staying here, I wanted to share my own honest experience. Location: The location is excellent. The hotel is directly across from the beautiful Bushnell Park and only about a 5-minute walk from downtown Hartford. Hotel: Yes, the hotel is older and definitely has an outdated feel. You may notice an old-carpet smell, but considering the age of the building, it wasn't a major issue for me. Room: I stayed in a Queen room, and overall, it was clean and well maintained. My only complaint was the lighting. The room was fairly dark, and I had to rely mostly on the lamps on the nightstands. Bathroom: The bathroom is also older and could definitely use an upgrade. However, it was clean and perfectly fine for taking a shower. One thing I did find inconvenient was that there were no electrical outlets in the bathroom. Breakfast: DELICIOUS! Definitely one of the highlights of my stay. Staff: The staff was welcoming, friendly, and attentive throughout my stay. Overall: Was it a modern, luxury hotel? No. Is the property showing its age? Absolutely. But it was clean, comfortable, conveniently located, and the staff was great. Based on some of the previous reviews, I expected much worse. My experience was actually quite positive, especially for a work trip."

Holiday Inn Express Southington by IHG

8/10 Good

"It was ok a little dated breakfast was pretty good coffee was excellent ..."

Hyatt Place Milford / New Haven

10/10 Excellent

"I felt happy the moment I checked in. Spacious clean room with wetbar, great view to back of property, housekeeping provided daily all essentials. Breakfast was great, plenty of parking, great interaction with staff"

More cheap stays in Cheshire