Search Middletown Villa Rentals from CA $100

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3
No exact matches found, but these alternatives could be just right

Recommended hotels in Middletown

A brick building with a sign that reads "Inn at Middletown."

1. Inn at Middletown

Inn at Middletown
3.5 star property
Washington Street Historic District
8.8 out of 10, Excellent, (680 reviews)
"We only stayed one night but were very happy with everything. Clean, great staff and very comfortable. Wish there might have been an option for continental breakfast included but the restaurant on the premises looked very nice too."
United States
Wendy
The price is CA $216
CA $277 total
includes taxes & fees
Dec 8 - Dec 9
Inn at Middletown
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

2. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (7 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is CA $143
CA $348 total
includes taxes & fees
Nov 9 - Nov 10
2BR Apartment Near Wesleyan 102
A modern kitchen with a central island, white cabinetry, stainless steel appliances, and a wooden floor.

3. 2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
9.6 out of 10, Exceptional, (4 reviews)
"The living quarters was clean, no bugs, essentials provided (except laundry detergent and hair dryer), quiet residence, muddy parking lot, safe neighborhood, great communication and ease of parking and entry. "
United States
Joanne L.
The price is CA $164
CA $395 total
includes taxes & fees
Nov 8 - Nov 9
2BR Apartment Near Wesleyan 301
A residential house with a garage, surrounded by trees and a clear sky.

4. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (34 reviews)
"Gilbert is an amazing host! I highly recommend staying here if you are visiting Middletown."
United States
Audrey F.
The price is CA $196
CA $364 total
includes taxes & fees
Dec 8 - Dec 9
Family Stays: Middletown, CT
A covered porch with a table and chairs, a doormat, and a view of trees and a house in the background.

5. Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101
Washington Street Historic District
7.2 out of 10, Good, (5 reviews)
"Very clean. No frills."
United States
Kristoph
The price is CA $143
CA $384 total
includes taxes & fees
Nov 9 - Nov 10
Private Apt in Middletown-Wesleyan 101
A wooden deck with a railing, overlooking a calm lake with autumn foliage.

6. #24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (27 reviews)
"It was great "
United States
Rodrigo C.
#24 *Serenity* A Lakefront Cottage Retreat
A modern living room with a leather sofa, a dining table with chairs, a kitchen area with white cabinets, and a chandelier.

7. #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.
The price is CA $291
CA $665 total
includes taxes & fees
Nov 23 - Nov 24
#29 - Modern 5 Bedroom/2 Bath
A modern hotel with multiple floors, large windows, and a sign for Springhill Suites.

8. Springhill Suites by Marriott Hartford Cromwell

Springhill Suites by Marriott Hartford Cromwell
2.5 star property
Cromwell
8.8 out of 10, Excellent, (796 reviews)
"Enjoyed my stay, I’ll be staying there again."
United States
David
The price is CA $209
CA $240 total
includes taxes & fees
Nov 22 - Nov 23
Springhill Suites by Marriott Hartford Cromwell
A large, stately building with symmetrical architecture, featuring multiple windows and a central entrance.

9. Courtyard by Marriott Hartford Cromwell

Courtyard by Marriott Hartford Cromwell
3.0 star property
Cromwell
8.6 out of 10, Excellent, (774 reviews)
"Excellent from check in to check out"
United States
Richard
The price is CA $178
CA $204 total
includes taxes & fees
Nov 29 - Nov 30
Courtyard by Marriott Hartford Cromwell
A hotel with a yellow facade, brick accents, and a large tree in front.

10. The Cromwell Inn

The Cromwell Inn
2.5 star property
Cromwell
6.8 out of 10, (58 reviews)
"Always one of the best places to stay in central Connecticut, my personal favorite."
United States
Donovan
The price is CA $130
CA $149 total
includes taxes & fees
Nov 8 - Nov 9
The Cromwell Inn
A Best Western Plus hotel with a two-story structure, multiple parking spaces, and a landscaped front yard.

11. Best Western Plus New England Inn & Suites

Best Western Plus New England Inn & Suites
2.5 star property
Berlin
8.6 out of 10, Excellent, (1,002 reviews)
"Needs a little updating but clean and staff good."
United States
Kellen
The price is CA $147
CA $169 total
includes taxes & fees
Nov 12 - Nov 13
Best Western Plus New England Inn & Suites
A Holiday Inn Express & Suites hotel with a covered entrance, stone facade, and a clear sky.

12. Holiday Inn Express & Suites Meriden by IHG

Holiday Inn Express & Suites Meriden by IHG
2.5 star property
Meriden
8.4 out of 10, Very good, (1,002 reviews)
"Hotel was clean, well appointed and friendly staff."
United States
John
The price is CA $133
CA $153 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express & Suites Meriden by IHG
A hotel room with a bed, two bedside tables, a chair, a desk, and a window with curtains.

13. Super 8 by Wyndham Cromwell/Middletown

Super 8 by Wyndham Cromwell/Middletown
2.0 star property
Cromwell
6.6 out of 10, (999 reviews)
"The staff was nice"
United States
Renee
The price is CA $100
CA $115 total
includes taxes & fees
Nov 15 - Nov 16
Super 8 by Wyndham Cromwell/Middletown
A Days Inn with a distinctive tower and a covered parking area.

14. Days Inn by Wyndham Berlin Meriden

Days Inn by Wyndham Berlin Meriden
2.0 star property
Berlin
7.0 out of 10, Good, (1,002 reviews)
"Great location, clean and quiet rooms"
United States
Chibueze
The price is CA $103
CA $119 total
includes taxes & fees
Nov 8 - Nov 9
Days Inn by Wyndham Berlin Meriden
A sunset over a body of water with a boat and a tree silhouetted against the sky.

15. Solano Inn

Solano Inn
2.5 star property
Portland
8.4 out of 10, Very good, (289 reviews)
"Very nice place to stay."
United States
Douglas
The price is CA $127
CA $146 total
includes taxes & fees
Nov 8 - Nov 9
Solano Inn
A Sheraton hotel with a modern design, featuring a prominent entrance, well-lit pathways, and landscaped surroundings.

16. Sheraton Hartford South Hotel

Sheraton Hartford South Hotel
3.5 star property
Rocky Hill
8.2 out of 10, Very good, (1,004 reviews)
"Clean facility, helpful staff. Easy on off highway, good location. Good place for dog walking. Be aware breakfast is not included in the price-not even coffee. Available $17 per person."
United States
Anne
The price is CA $147
CA $169 total
includes taxes & fees
Nov 15 - Nov 16
Sheraton Hartford South Hotel
A Hampton Inn & Suites building with a clear entrance, a parking lot, and a flagpole.

17. Hampton Inn & Suites Rocky Hill - Hartford South

Hampton Inn & Suites Rocky Hill - Hartford South
2.5 star property
Rocky Hill
9.2 out of 10, Wonderful, (910 reviews)
"Overall good for a short stay"
United States
Alyssa
The price is CA $171
CA $197 total
includes taxes & fees
Nov 15 - Nov 16
Hampton Inn & Suites Rocky Hill - Hartford South
A Howard Johnson motel with a large American flag, a signboard, and a wooden chair in the foreground.

18. Howard Johnson by Wyndham Hartford South – Rocky Hill

Howard Johnson by Wyndham Hartford South – Rocky Hill
2.0 star property
Rocky Hill
8.2 out of 10, Very good, (1,003 reviews)
"We had a great stay here. The staff were super kind and the rooms were clean"
United States
Emily
The price is CA $104
CA $120 total
includes taxes & fees
Nov 22 - Nov 23
Howard Johnson by Wyndham Hartford South – Rocky Hill
A hotel with a red neon sign, multiple floors, and a covered entrance.

19. Red Roof Inn Meriden

Red Roof Inn Meriden
2.0 star property
Meriden
7.6 out of 10, Good, (1,003 reviews)
"We've stayed here before, and were very happy with our experience. Very quiet, clean, and safe. The staff are great too!!"
United States
Adrienne
The price is CA $132
CA $152 total
includes taxes & fees
Nov 8 - Nov 9
Red Roof Inn Meriden
A Fairfield hotel with a modern facade, a covered entrance, and well-maintained landscaping.

20. Fairfield by Marriott Inn & Suites Wallingford New Haven

Fairfield by Marriott Inn & Suites Wallingford New Haven
3.0 star property
Wallingford
8.6 out of 10, Excellent, (1,002 reviews)
"The hotel was very nice, a comfortable room, nice staff, good breakfast, very convenient location (a minute from the highway) and a reasonable price."
United States
Susie
The price is CA $175
CA $202 total
includes taxes & fees
Nov 22 - Nov 23
Fairfield by Marriott Inn & Suites Wallingford New Haven
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

Learn more about Middletown

Wesleyan University's stunning campus and the Connecticut River waterfront offer perfect spots for afternoon strolls and picnics. Explore Main Street's indie bookshops and farm-to-table restaurants, then catch a show at the historic Oddfellows Playhouse where locals gather.

See all hotels in Middletown
A coastal cityscape with a marina, dense urban buildings, and a river.

Top reviews in Middletown

A modern hotel with multiple floors, large windows, and a sign for Springhill Suites.
Springhill Suites by Marriott Hartford Cromwell

Springhill Suites by Marriott Hartford Cromwell

Springhill Suites by Marriott Hartford Cromwell
Cromwell

10/10 Excellent

Solid
Canada
Chris
Reviewed April 7, 2026
Springhill Suites by Marriott Hartford Cromwell

Frequently Asked Questions

Why book your villa in Middletown with Expedia?

Expedia makes it a breeze to find your ideal villa in Middletown. Vacationing with the family? Use our filters to search for stays with a kitchen or a pool. If you're sticking to a budget, select how much you'd like to spend and the star rating of the property. We'll help you find the perfect pad that gels with your taste and style.

How can I find cheap villas in Middletown?

Expedia is here to help you narrow your search for cheap villas in Middletown. Simply use our convenient filter tool to select budget, amenities and star rating to refine your search and find the perfect stay in a few quick clicks.

What is there to do near my villa in Middletown?

After you've checked in to your villa, head out and discover the cool things Middletown has on offer. Kidcity Children's Museum is a popular attraction to add to your itinerary.

Explore a world of travel with Expedia