A steel bridge with a truss design spanning over a calm river, surrounded by lush greenery.

Cromwell Holiday Rentals

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Our top choices for Cromwell holiday rentals

1. Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
The price is NZ$1,537
includes taxes & fees
18 Aug - 19 Aug
Conference Room Rental no sleeping arrangements

2. 2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
10.0 out of 10, Exceptional, (3 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 NZ$471
includes taxes & fees
18 Aug - 19 Aug
2BR Apartment Near Wesleyan 301

3. #24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (25 reviews)
"It was great "
United States
Rodrigo C.
The price is NZ$598
includes taxes & fees
18 Aug - 19 Aug
#24 *Serenity* A Lakefront Cottage Retreat

4. 3 BR Apartment Near Wesleyan 202

3 BR Apartment Near Wesleyan 202
Washington Street Historic District
8.0 out of 10, Very good, (1 review)
"The apartment is the first floor of a two story duplex. It was very clean and larger than we were expecting. We had just about everything we needed for our stay. We really appreciate being able to bring our pets with us. I enjoyed walking around the neighborhood with my dog."
United States
Douglas M.
The price is NZ$638
includes taxes & fees
18 Aug - 19 Aug
3 BR Apartment Near Wesleyan 202

5. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
8.8 out of 10, Excellent, (5 reviews)
The price is NZ$420
includes taxes & fees
18 Aug - 19 Aug
2BR Apartment Near Wesleyan 102

6. “3BR Home Near Wesleyan & Downtown Middletown

“3BR Home Near Wesleyan & Downtown Middletown
Washington Street Historic District
7.8 out of 10, Good, (6 reviews)
"Nice place"
United States
Jousette C.
The price is NZ$492
includes taxes & fees
31 Aug - 1 Sept
“3BR Home Near Wesleyan & Downtown Middletown

7. 3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
10.0 out of 10, Exceptional, (1 review)
"Clean apartment plenty of parking"
United States
Rebecca P.
The price is NZ$540
includes taxes & fees
18 Aug - 19 Aug
3 BR Apartment Near Wesleyan 201

8. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (181 reviews)
"Great property for quiet and a nice getaway. Great little places to eat and shop in the surrounding towns."
United States
Frank
The price is NZ$420
includes taxes & fees
16 Sept - 17 Sept
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

9. Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101
Washington Street Historic District
7.0 out of 10, Good, (4 reviews)
"Very clean. No frills."
United States
Kristoph
The price is NZ$471
includes taxes & fees
18 Aug - 19 Aug
Private Apt in Middletown-Wesleyan 101

10. Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Middletown
9.8 out of 10, Exceptional, (17 reviews)
"Large, comfortable house in a tranquil part of town. "
United States
Daryl R.
The price is NZ$1,517
includes taxes & fees
31 Aug - 1 Sept
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

11. Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.0 out of 10, Wonderful, (7 reviews)
"Clean, convenient, and great location."
United States
Shaun L.
The price is NZ$516
includes taxes & fees
9 Sept - 10 Sept
Private Apartment in Berlin

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

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (35 reviews)
"My son and I were here for two nights and had an excellent time. It was exactly as described and such a tastefully decorated and maintained place to stay. Would definitely stay here again if in the area!"
United States
Kate F.
The price is NZ$434
includes taxes & fees
24 Aug - 25 Aug
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

13. Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment

Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
New Britain
6.8 out of 10, (8 reviews)
" Not bad for the price "
United States
Audrey L.
The price is NZ$642
includes taxes & fees
13 Sept - 14 Sept
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment

14. Lakeview Carriage House with Spectacular Sunset Views

Lakeview Carriage House with Spectacular Sunset Views
Lake Pocotopaug
10.0 out of 10, Exceptional, (19 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is NZ$525
includes taxes & fees
7 Sept - 8 Sept
Lakeview Carriage House with Spectacular Sunset Views

15. New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Durham
9.8 out of 10, Exceptional, (30 reviews)
"Wonderful house in a great location."
United States
Edward S.
The price is NZ$1,745
includes taxes & fees
18 Aug - 19 Aug
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

16. Cozy basement apartment with private bathroom, kitchen and entrance.

Cozy basement apartment with private bathroom, kitchen and entrance.
Marlborough
The price is NZ$839
includes taxes & fees
25 Aug - 26 Aug
Cozy basement apartment with private bathroom, kitchen and entrance.

17. Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (4 reviews)
"the place was clean bed was nice"
United States
Jonathan
The price is NZ$278
includes taxes & fees
18 Aug - 19 Aug
Humble Abode #2

18. The Game House Arcade – West Hartford

The Game House Arcade – West Hartford
West Hartford
10.0 out of 10, Exceptional, (1 review)
"Great location and well equipped. We will be back"
United States
Mike W.
The price is NZ$802
includes taxes & fees
18 Aug - 19 Aug
The Game House Arcade – West Hartford

19. Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen

Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen
Manchester Center
10.0 out of 10, Exceptional, (10 reviews)
"Nice private place to stay."
United States
Brian A.
The price is NZ$262
includes taxes & fees
31 Aug - 1 Sept
Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen

20. Premier League Pad - with Free Parking, Heat & AC

Premier League Pad - with Free Parking, Heat & AC
Manchester
10.0 out of 10, Exceptional, (3 reviews)
"Perfect place to stay if you need to stay in Manchester. The apartment was so clean and accommodating. The host was very easy to communicate with! I would gladly stay here again!"
United States
Corey J.
The price is NZ$413
includes taxes & fees
20 Aug - 21 Aug
Premier League Pad - with Free Parking, Heat & AC
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cromwell Hotel Reviews

Find out more about Cromwell

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cromwell holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cromwell. 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 Cromwell. Seeing all the best attractions is bound to make you fall in love with Cromwell. Who knows, you may even be tempted to extend your 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 holiday 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 Cromwell short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Cromwell?

Yes, there are holiday rentals close to the most popular sights in Cromwell, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Cromwell. While you're here, grab a bite or have a drink at the coffee shops.

What are some of the best holiday rentals that Cromwell has to offer?

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville: This holiday home rental outside of Cromwell is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

What’s there to see and do in Cromwell?

Connecticut River State Wildlife Area and Connecticut River are a couple of lovely local spots to get outside and enjoy nature. TPC River Highlands and Cromwell Commons Shopping Center are other places to visit while you're in town.

What’s a holiday rental in Cromwell like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cromwell. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for families.