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

Cromwell Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Cromwell vacation rentals

A modern office space with a sofa, two round tables, and a coffee table. There are chairs around the tables, a rug on the floor, and a door in the background.

1. Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
$823 nightly
The price is $931
Sep 25 - Sep 26
Total with taxes and fees
Conference Room Rental no sleeping arrangements
A wooden deck with chairs overlooking a calm lake surrounded by autumn foliage.

2. #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.
$317 nightly
The price is $341
Sep 28 - Sep 29
Total with taxes and fees
#24 Serenity A Lakefront Cottage Retreat
A compact kitchen with white cabinets, a built-in oven, and a dining table with chairs.

3. 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
$261 nightly
The price is $296
Oct 5 - Oct 6
Total with taxes and fees
Private Apt in Middletown-Wesleyan 101

4. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (30 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
$224 nightly
The price is $255
Sep 29 - Sep 30
Total with taxes and fees
Family Stays: Middletown, CT
A dining room with a rectangular table and four chairs, a window with blinds, a recessed ceiling light, and a wall-mounted air conditioning unit.

5. 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.
3 BR Apartment Near Wesleyan 202
A compact kitchen with wooden walls, a window with a view of greenery, a built-in dishwasher, and a sink.

6. 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, (191 reviews)
"Beautiful cabin! Will def go again!"
United States
Morainny
$167 nightly
The price is $192
Sep 29 - Sep 30
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

7. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (6 reviews)
"Excellent beds and clean."
United States
DANIEL M.
$228 nightly
The price is $258
Sep 27 - Sep 28
Total with taxes and fees
2BR Apartment Near Wesleyan 102
A wooden deck with wicker furniture, white railings, and a gazebo in the background.

8. Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin
Berlin
8.0 out of 10, Very good, (2 reviews)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
$287 nightly
The price is $325
Sep 28 - Sep 29
Total with taxes and fees
Soothing 2-bedroom lower-level apartment in Berlin
A modern kitchen with dark cabinetry, a marble countertop, and a dining area with a table and chairs.

9. 3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Clean apartment plenty of parking"
United States
Rebecca P.
$281 nightly
The price is $318
Sep 28 - Sep 29
Total with taxes and fees
3 BR Apartment Near Wesleyan 201
A modern living room with a sofa, a dining table, and a massage chair.

10. #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.
$468 nightly
The price is $501
Oct 7 - Oct 8
Total with taxes and fees
#29 - Modern 5 Bedroom/2 Bath

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.
$232 nightly
The price is $264
Sep 27 - Sep 28
Total with taxes and fees
Private Apartment in Berlin
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a coffee table. There is a kitchen in the background with white cabinets and a wooden countertop.

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, (37 reviews)
"We had a great stay, very clean and cozy! Our host was very nice and responsive. Great location, would definitely recommend!!!"
United States
Kristy C.
$236 nightly
The price is $267
Oct 20 - Oct 21
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A modern living room with a glass dining table, dark chairs, a sofa, and a ceiling fan.

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.
$324 nightly
The price is $366
Sep 27 - Sep 28
Total with taxes and fees
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

14. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
$276 nightly
The price is $294
Oct 5 - Oct 6
Total with taxes and fees
Newly Remodeled 1-BR Close to Everything yet Very Private
A hallway with a patterned wall, a wooden floor, a rug, a door with a wreath, and a bed visible through a glass door.

15. The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
9.0 out of 10, Wonderful, (26 reviews)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
$236 nightly
The price is $251
Oct 7 - Oct 8
Total with taxes and fees
The Sun Filled Cozy Creamery
A brick building with the sign "CELY ARTS ON PEARL" and a red awning.

16. Simple Comfort and Tranquility

Simple Comfort and Tranquility
New Britain
Simple Comfort and Tranquility
A living room with a grey sofa, yellow cushions, a wooden coffee table, a TV on a stand, and a lamp on a side table.

17. Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
$274 nightly
The price is $292
Sep 25 - Sep 26
Total with taxes and fees
Newly Remodeled with deck. Close to town center
A two-story house with a front porch, a garage, and a well-maintained lawn.

18. 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
9.6 out of 10, Exceptional, (19 reviews)
"The house was exactly what we were looking for, for a weekend away. Will surely book again, thank you!"
United States
Lee S.
$733 nightly
The price is $829
Sep 28 - Sep 29
Total with taxes and fees
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

19. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (14 reviews)
"This apartment was wonderful - clean, well stocked, and cute. Aside from the proximity to the train tracks (although earplugs were thoughtfully provided), the location was great - close to the highway and more importantly Dairy Queen."
United States
Becky P.
$274 nightly
The price is $292
Sep 27 - Sep 28
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
A modern living room with a blue sofa, a coffee table, and a dining area with a kitchen in the background.

20. #23 COMFORT & LUXURY 3 BR/2 BA House

#23 COMFORT & LUXURY 3 BR/2 BA House
Southington
9.8 out of 10, Exceptional, (9 reviews)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
$348 nightly
The price is $374
Oct 7 - Oct 8
Total with taxes and fees
#23 COMFORT & LUXURY 3 BR/2 BA House
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

Best Western Plus New England Inn & Suites

Best Western Plus New England Inn & Suites

10/10 Excellent
"Stuff was helpful and rooms clean"
Dursun 1-night trip
Posted 5 hours ago
Best Western Plus New England Inn & Suites

Find out more about Cromwell

Everything you need to know about Cromwell 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 Cromwell 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 Cromwell vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cromwell vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cromwell. 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 Cromwell 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 $192 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 Cromwell rentals

At Expedia, we put the best Cromwell 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 Cromwell 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 Cromwell 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 Cromwell. 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

Frequently asked questions

Can I find vacation rentals in Cromwell?

Yes, we give you a choice of vacation rentals close to well known attractions in Cromwell, or you can go with a more secluded option if you'd like a relaxing place to stay. Visitors like the top-notch restaurants and shops in Cromwell. While you're here, grab a bite or have a drink at the coffeehouses.

What's the top vacation rental in Cromwell?

Cabin Love at the Lake: This vacation home rental outside of Cromwell offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What’s there to see and do in Cromwell?

Connecticut River and Connecticut River State Wildlife Area 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 vacation rental in Cromwell like?

Vacation rentals are privately owned properties you can reserve for a couple days or more in Cromwell. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family getaway.