Cromwell Holiday Rentals

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Check prices for these dates

Tonight
21 Dec - 22 Dec
Tomorrow
22 Dec - 23 Dec
Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan

Our top choices for Cromwell holiday rentals

Fridge, stovetop, coffee/tea maker, toaster
Charming New England Tiny Home in Cromwell, CT

Apartment in Main Street Historic District

Charming New England Tiny Home in Cromwell, CT
10.0 out of 10, Exceptional, (1)
"It was the perfect escape- close enough to home but just far enough to feel like a vacation, the whole process was 10 out of 10 and def worth a 2nd stay!"
United States
Amanda G.
Charming New England Tiny Home in Cromwell, CT
Interior
Conference Room Rental no sleeping arrangements

Apartment in Main Street Historic District

Conference Room Rental no sleeping arrangements
The price is HK$5,602
HK$7,244 total
includes taxes & fees
23 Dec - 24 Dec
Conference Room Rental no sleeping arrangements
Exterior
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Cabin in East Haddam

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
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
The price is HK$787
HK$1,263 total
includes taxes & fees
4 Jan - 5 Jan 2026
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Property grounds
Humble Abode #2

Apartment in Manchester Center

Humble Abode #2
2.0 star property
10.0 out of 10, Exceptional, (1)
"the place was clean bed was nice"
United States
Jonathan
The price is HK$934
HK$1,229 total
includes taxes & fees
29 Dec - 30 Dec
Humble Abode #2
Fridge, microwave, oven, stovetop
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Apartment in Cheshire

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
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.
The price is HK$658
HK$1,271 total
includes taxes & fees
23 Dec - 24 Dec
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Outdoor dining
The Historic Hideaway

Apartment in Avon

The Historic Hideaway
2.0 star property
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.
The price is HK$428
HK$1,897 total
includes taxes & fees
9 Jan - 10 Jan 2026
The Historic Hideaway
Dining
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Cabin in Coventry Lake

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
9.4 out of 10, Exceptional, (39)
"Pet and family, friendly"
United States
Mary-Kate G
The price is HK$949
HK$2,212 total
includes taxes & fees
28 Dec - 29 Dec
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Exterior
The Blue Back Bungalow

Apartment in West Hartford

The Blue Back Bungalow
2.0 star property
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.
The price is HK$630
HK$2,430 total
includes taxes & fees
30 Dec - 31 Dec
The Blue Back Bungalow
TV
Heart of Hartford: 1-BR by Convention|XLCenter

Apartment in Downtown Hartford

Heart of Hartford: 1-BR by Convention|XLCenter
The price is HK$716
HK$1,833 total
includes taxes & fees
19 Jan - 20 Jan 2026
Heart of Hartford: 1-BR by Convention|XLCenter
Interior
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Holiday Home in Coventry Lake

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
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.
The price is HK$926
HK$2,115 total
includes taxes & fees
27 Dec - 28 Dec
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
TV
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Holiday Home in New Britain

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
10.0 out of 10, Exceptional, (8)
" Heck-on was smooth and the kitchen and facilities were great. "
United States
Elizabeth P.
The price is HK$875
HK$1,917 total
includes taxes & fees
5 Jan - 6 Jan 2026
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
TV
Modern Living: 1-BR Near XLCenter|ConventionCenter

Apartment in Downtown Hartford

Modern Living: 1-BR Near XLCenter|ConventionCenter
The price is HK$599
HK$1,486 total
includes taxes & fees
23 Dec - 24 Dec
Modern Living: 1-BR Near XLCenter|ConventionCenter
Property grounds
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Cabin in Coventry Lake

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
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.
The price is HK$1,175
HK$2,518 total
includes taxes & fees
4 Jan - 5 Jan 2026
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Interior
Fully Furnished Modern Private Studio in Hartford with AC / GYM Free Parking!

Apartment in Downtown Hartford

Fully Furnished Modern Private Studio in Hartford with AC / GYM Free Parking!
2.0 star property
The price is HK$700
HK$1,543 total
includes taxes & fees
27 Dec - 28 Dec
Fully Furnished Modern Private Studio in Hartford with AC / GYM Free Parking!
Smart TV, computer monitors
Central Chic Pad - with Free Parking, Heat & AC

Apartment in Manchester

Central Chic Pad - with Free Parking, Heat & AC
9.6 out of 10, Exceptional, (7)
"Great stay. Gas stove was a highlight!"
United States
Domenic
The price is HK$671
HK$1,636 total
includes taxes & fees
5 Jan - 6 Jan 2026
Central Chic Pad - with Free Parking, Heat & AC
Fridge, microwave, oven, stovetop
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Holiday Home in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in 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.
The price is HK$679
HK$3,845 total
includes taxes & fees
4 Jan - 5 Jan 2026
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Fridge, microwave, stovetop, coffee/tea maker
Charming Luxury 1BR Near Downtown. Dog Friendly!

Apartment in Manchester

Charming Luxury 1BR Near Downtown. Dog Friendly!
9.4 out of 10, Exceptional, (11)
"Had a nice stay at this VRBO. Cozy and quiet."
United States
James C.
Charming Luxury 1BR Near Downtown. Dog Friendly!
Dining
#24 *Serenity* A Lakefront Cottage Retreat

Holiday Home in Middletown

#24 *Serenity* A Lakefront Cottage Retreat
9.8 out of 10, Exceptional, (21)
"We had a wonderful stay at this property! The house itself was beautiful—spacious, clean, and incredibly comfortable. The setting was just as impressive, offering peaceful views and a great atmosphere to relax and unwind. Everything was exactly as described, if not better. We would absolutely stay here again and highly recommend it to anyone looking for a serene and well-appointed home base for our stay. "
United States
Nichole N.
The price is HK$2,716
HK$4,578 total
includes taxes & fees
31 Dec - 1 Jan 2026
#24 *Serenity* A Lakefront Cottage Retreat
Dining
Crested One Place - with Free Parking, Heat & AC

Apartment in Manchester

Crested One Place - with Free Parking, Heat & AC
The price is HK$671
HK$1,620 total
includes taxes & fees
12 Jan - 13 Jan 2026
Crested One Place - with Free Parking, Heat & AC
1 bedroom, iron/ironing board, WiFi, bed sheets
Once the old Schools house now a newly furnished Apartment

Holiday Home in Wallingford Center

Once the old Schools house now a newly furnished Apartment
9.0 out of 10, Wonderful, (13)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is HK$895
HK$2,243 total
includes taxes & fees
2 Jan - 3 Jan 2026
Once the old Schools house now a newly furnished Apartment
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

Courtyard by Marriott Hartford Cromwell

Courtyard by Marriott Hartford Cromwell

10/10 Excellent
"We had a wonderful stay; the staff were super friendly and the room was spotless. "
ANDERSON 2-night trip
Posted 21 hours ago
Courtyard by Marriott Hartford Cromwell

Find out more about Cromwell

Search for holiday rentals in Cromwell on Expedia! You can easily find your home rentals, villas, holiday apartments in Cromwell using one of the methods below:

  • View our selection of featured holiday rentals in Cromwell
  • Use the map to find apartments and other holiday homes in the Cromwell neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cromwell while they last

Look no further and take a look at our great range of rental properties in Cromwell!

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?

Private Apartment in Berlin: This holiday 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 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.