Middlefield Holiday Rentals

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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Middlefield holiday rentals

View from property

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, (108 reviews)
"Staff was sooo helpful that stood out the most honestly I loved it I’ll book again definitely "
United States
Aliah
The price is HK$851
HK$1,338 total
includes taxes & fees
3 Feb - 4 Feb
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
1 bedroom, desk, iron/ironing board, travel cot

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (34 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is HK$866
HK$1,698 total
includes taxes & fees
3 Feb - 4 Feb
1-bedroom cottage with Grove Beach 🏖️ access.
Property grounds

Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (1 review)
"the place was clean bed was nice"
United States
Jonathan
The price is HK$937
HK$1,233 total
includes taxes & fees
9 Feb - 10 Feb
Humble Abode #2
Cookware/dishes/utensils

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
East Rock
9.8 out of 10, Exceptional, (11 reviews)
"Thanks to the detailed information from the host check-in couldn’t have been easier. The home was clean and well-appointed. Great location with access to the Yale tram and local markets and restaurants. "
United States
Denyce D.
The price is HK$593
HK$1,884 total
includes taxes & fees
1 Feb - 2 Feb
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (21 reviews)
"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$1,187
HK$2,645 total
includes taxes & fees
18 Feb - 19 Feb
#24 *Serenity* A Lakefront Cottage Retreat
Beach

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is HK$1,023
HK$3,890 total
includes taxes & fees
4 Feb - 5 Feb
Beachside Bliss w/ Game Room, Gym & Golf Green
Terrace/patio

Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin
Berlin
10.0 out of 10, Exceptional, (1 review)
"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.
The price is HK$941
HK$2,478 total
includes taxes & fees
2 Feb - 3 Feb
Soothing 2-bedroom lower-level apartment in Berlin
Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (20 reviews)
"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"
United States
Harmony R.
The price is HK$937
HK$1,795 total
includes taxes & fees
2 Feb - 3 Feb
Family Stays: Middletown, CT
Property grounds

The little Chestnut. A charming historic apartment in Downtown Chester

The little Chestnut. A charming historic apartment in Downtown Chester
Chester Center
10.0 out of 10, Exceptional, (6 reviews)
"A lovely little place! Everything we needed, in a great location."
United States
Michael S.
The price is HK$1,266
HK$2,839 total
includes taxes & fees
1 Feb - 2 Feb
The little Chestnut. A charming historic apartment in Downtown Chester
Smart TV

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

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.2 out of 10, Wonderful, (15 reviews)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is HK$773
HK$1,404 total
includes taxes & fees
18 Feb - 19 Feb
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Interior

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
Manchester Center
10.0 out of 10, Exceptional, (6 reviews)
"Cute, comfortable, quiet accommodation. It was perfect for our visit to Hartford. "
United States
Diana V.
The price is HK$937
HK$1,548 total
includes taxes & fees
2 Feb - 3 Feb
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
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
Southington
10.0 out of 10, Exceptional, (1 review)
"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$766
HK$3,986 total
includes taxes & fees
6 Feb - 7 Feb
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Dining

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Clinton
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is HK$1,046
HK$4,046 total
includes taxes & fees
10 Feb - 11 Feb
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Interior

Nautical 3BR Sleeps 8 @ Tweed Airport W/ Fire Pit + Smart TVs Near Beach & Yale

Nautical 3BR Sleeps 8 @ Tweed Airport W/ Fire Pit + Smart TVs Near Beach & Yale
East Shore
10.0 out of 10, Exceptional, (1 review)
"Had a Great stay at the nauti nook!"
United States
David D.
The price is HK$1,049
HK$3,443 total
includes taxes & fees
2 Feb - 3 Feb
Nautical 3BR Sleeps 8 @ Tweed Airport W/ Fire Pit + Smart TVs Near Beach & Yale
Interior

Cozy Guest Suite in Historic Home

Cozy Guest Suite in Historic Home
Middletown
10.0 out of 10, Exceptional, (1 review)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is HK$1,152
HK$1,676 total
includes taxes & fees
1 Feb - 2 Feb
Cozy Guest Suite in Historic Home
Exterior

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6 reviews)
"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."
United States
Veronica
The price is HK$1,132
HK$2,713 total
includes taxes & fees
3 Feb - 4 Feb
Angelica’s safe haven @ west haven
Smart TV

Cozy East Haven Home • Near Beach & Yale

Cozy East Haven Home • Near Beach & Yale
Momauguin
10.0 out of 10, Exceptional, (5 reviews)
"Such a cute place, loved all the nautical touches. Great space for a weekend getaway, pretty well-stocked kitchen, clean & cozy. Really appreciated the outdoor space & amenities too! And Michael the host is very responsive & helpful! "
United States
Amal A.
The price is HK$878
HK$1,166 total
includes taxes & fees
10 Feb - 11 Feb
Cozy East Haven Home • Near Beach & Yale
Smart TV

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, (16 reviews)
"House was great & close to where we needed to be. "
United States
Erica M.
The price is HK$929
HK$2,185 total
includes taxes & fees
2 Feb - 3 Feb
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Interior

The Nest At Elm City Flats.

The Nest At Elm City Flats.
West New Haven
9.6 out of 10, Exceptional, (7 reviews)
"We had a great stay at this apartment. You do have to go up three flight of stairs but thankfully we were able to climb them. "
United States
Joan S.
The price is HK$696
HK$1,840 total
includes taxes & fees
6 Feb - 7 Feb
The Nest At Elm City Flats.
Smart TV, fireplace, books, music library

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, (28 reviews)
"Fantastic experience from beginning to end! Loved every minute of my stay! "
United States
Jody U.
The price is HK$976
HK$1,998 total
includes taxes & fees
6 Feb - 7 Feb
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
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 Middlefield Hotel Reviews

New Haven Hotel

New Haven Hotel

10/10 Excellent
"Clean and comfortable "
Ronald 3-night trip
Posted 2 days ago
New Haven Hotel

Find out more about Middlefield

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

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

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

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Frequently asked questions

Can I find a holiday rental in Middlefield?

Yes, there are holiday rentals close to the most popular sights in Middlefield, or you can select a more secluded option if you're looking for a relaxing stay. Middlefield is known for its golf courses and waterfalls. Make sure you have time to check out the ski areas and restaurants during your trip.

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

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage: This holiday home rental outside of Middlefield offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Middlefield?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Middlefield stay.

What’s there to see and do in Middlefield?

Lake Beseck Beach and Wadsworth Falls State Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Lyman Orchards and Powder Ridge Mountain Park and Resort.

What’s a holiday rental in Middlefield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middlefield. Holiday rentals provide amenities like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for small groups.