Cromwell Vacation Rentals

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In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Cromwell vacation rentals

Interior
Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
$823 nightly
The price is $931
Dec 26 - Dec 27
Total with taxes and fees
Conference Room Rental no sleeping arrangements
Exterior
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
East Haddam
9.6 out of 10, Exceptional, (93)
"My wife loved it…she has a rough week with work and just life in general, so I wanted to do something nice for her and surprised her with a stay here…she was really happy and loved everything about it…can’t wait to do this again 😊"
United States
Keven
$159 nightly
The price is $183
Jan 4 - Jan 5, 2026
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Interior
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (34)
"We were in town for a family event and the cottage was a perfect choice!Very comfortable, well appointed and just steps from the lake!I'll definitely book again next time I'm in town!"
United States
George J.
$254 nightly
The price is $287
Jan 4 - Jan 5, 2026
Total with taxes and fees
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Fridge, microwave, oven, stovetop
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

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

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.4 out of 10, Exceptional, (13)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
$145 nightly
The price is $163
Jan 14 - Jan 15, 2026
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Dining
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
9.4 out of 10, Exceptional, (39)
"Pet and family, friendly"
United States
Mary-Kate G
$248 nightly
The price is $281
Dec 28 - Dec 29
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Exterior
The Blue Back Bungalow

The Blue Back Bungalow

The Blue Back Bungalow
2.0 star property
West Hartford
9.4 out of 10, Exceptional, (18)
"The stay was good. The house is located in a great area and very close to my family member we were visiting. I will stay again and make sure everything is in order. "
United States
Vanessia P.
$297 nightly
The price is $314
Dec 30 - Dec 31
Total with taxes and fees
The Blue Back Bungalow
Fridge, microwave, oven, stovetop
Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
10.0 out of 10, Exceptional, (5)
"This house was perfect for the 4 of us. We all had our own bedroom and shared the bath. It’s very clean and close to everywhere we were going! The home is modern and the beds were comfy! I would stay there again. Great home! "
United States
Lorie D.
$250 nightly
The price is $283
Dec 27 - Dec 28
Total with taxes and fees
Modern & Cozy Cape | 4 Bedroom House | Central Location
Property grounds
Humble Abode #2

Humble Abode #2

Humble Abode #2
2.0 star property
Manchester Center
10.0 out of 10, Exceptional, (1)
"the place was clean bed was nice"
United States
Jonathan
$140 nightly
The price is $158
Jan 1 - Jan 2, 2026
Total with taxes and fees
Humble Abode #2
Property grounds
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
8.8 out of 10, Excellent, (48)
"Very nice place to get away and enjoy the lake! Host responded very quickly and was very helpful! Would book again. "
United States
Rachel G.
$260 nightly
The price is $294
Jan 4 - Jan 5, 2026
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Fridge, microwave, oven, stovetop
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

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

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (1)
"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
Cindy M.
$436 nightly
The price is $494
Jan 4 - Jan 5, 2026
Total with taxes and fees
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Outdoor dining
The Historic Hideaway

The Historic Hideaway

The Historic Hideaway
2.0 star property
Avon
7.0 out of 10, Good, (2)
"House exactly as listed. We had a question and the property owner replied instantly - great communication. Close to Talcott Mountain which was an amazing hike with beautiful views. "
United States
Nicole M.
$232 nightly
The price is $244
Jan 9 - Jan 10, 2026
Total with taxes and fees
The Historic Hideaway
Smart TV
Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
2.0 star property
South Windsor
$97 nightly
The price is $108
Jan 1 - Jan 2, 2026
Total with taxes and fees
Entire guest suite in South Windsor, Connecticut
TV
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
New Britain
10.0 out of 10, Exceptional, (8)
" Heck-on was smooth and the kitchen and facilities were great. "
United States
Elizabeth P.
$218 nightly
The price is $246
Jan 5 - Jan 6, 2026
Total with taxes and fees
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
Smart TV, computer monitors
Central Chic Pad - with Free Parking, Heat & AC

Central Chic Pad - with Free Parking, Heat & AC

Central Chic Pad - with Free Parking, Heat & AC
Manchester
9.6 out of 10, Exceptional, (7)
"Great stay. Gas stove was a highlight!"
United States
Domenic
$197 nightly
The price is $210
Jan 5 - Jan 6, 2026
Total with taxes and fees
Central Chic Pad - with Free Parking, Heat & AC
Outdoor dining
Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin
Berlin
10.0 out of 10, Exceptional, (1)
"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.
$285 nightly
The price is $323
Jan 5 - Jan 6, 2026
Total with taxes and fees
Soothing 2-bedroom lower-level apartment in Berlin
Smart TV
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester

Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester

Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
2.0 star property
Manchester Center
10.0 out of 10, Exceptional, (5)
"Cute, comfortable, quiet accommodation. It was perfect for our visit to Hartford. "
United States
Diana V.
$163 nightly
The price is $184
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
Fridge, microwave, oven, stovetop
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
9.4 out of 10, Exceptional, (14)
"House was great & close to where we needed to be. "
United States
Erica M.
$236 nightly
The price is $267
Jan 5 - Jan 6, 2026
Total with taxes and fees
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Exterior
Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center
Wallingford
10.0 out of 10, Exceptional, (2)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
$271 nightly
The price is $288
Jan 3 - Jan 4, 2026
Total with taxes and fees
Newly Remodeled with deck. Close to town center
Fridge, microwave, oven, stovetop
Family Stays: Middletown, CT

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (19)
"The house was great, the welcome snacks and balloons were thoughtful and the kitchen coffee, etc, was much appreciated. This was an excellent stay and I highly recommend it!"
United States
Cari M.
$209 nightly
The price is $237
Jan 6 - Jan 7, 2026
Total with taxes and fees
Family Stays: Middletown, CT
Interior
Cozy Guest Suite in Historic Home

Cozy Guest Suite in Historic Home

Cozy Guest Suite in Historic Home
Middletown
10.0 out of 10, Exceptional, (1)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
$190 nightly
The price is $215
Jan 3 - Jan 4, 2026
Total with taxes and fees
Cozy Guest Suite in Historic Home
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

The Farmington Inn & Suites

The Farmington Inn & Suites

10/10 Excellent
"Love the inn"
Donna 3-night trip
Posted 3 days ago
The Farmington 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 $152 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?

Private Apartment in Berlin: This vacation home rental outside of Cromwell is equipped with a balcony, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.