A waterfall in a forested area with a rocky ledge and a calm pool at the base.

Middlefield Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Middlefield vacation rentals

A modern kitchen with a central island, white cabinetry, stainless steel appliances, and a wooden floor.

1. 2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
9.6 out of 10, Exceptional, (4 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 ￥17,066
￥46,331 total
includes taxes & fees
Oct 20 - Oct 21
2BR Apartment Near Wesleyan 301
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

2. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (7 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is ￥19,626
￥45,277 total
includes taxes & fees
Oct 18 - Oct 19
2BR Apartment Near Wesleyan 102
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.

3. 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, (39 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.
The price is ￥19,753
￥41,520 total
includes taxes & fees
Oct 27 - Oct 28
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Veterans Park, near the house

4. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (33 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
The price is ￥22,123
￥40,888 total
includes taxes & fees
Nov 17 - Nov 18
Family Stays: Middletown, CT
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

5. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and comfortable with easy communication with host I recommend this unit to all who want to visit Wallingford or who desire to take the train to ny or Boston etc"
United States
DAVID B.
The price is ￥18,656
￥46,118 total
includes taxes & fees
Oct 28 - Oct 29
All New Studio apartment in center of town
A cabin with a dining table set for two, a bicycle, and a small porch area.

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, (204 reviews)
"Great experience and the perfect environment"
United States
Stephanie
The price is ￥20,069
￥30,348 total
includes taxes & fees
Nov 16 - Nov 17
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A kitchen with dark cabinets, a granite countertop, a black stove, a microwave, and a sink.

7. Fully Furnished 1BR Apartment

Fully Furnished 1BR Apartment
Wallingford
10.0 out of 10, Exceptional, (4 reviews)
"This property was very clean and comfortable; a nicely remodeled apartment in an older home. We had family members staying in one of the other apartments, so it was great to have them so close, but still had privacy. The location is conveniently located with plenty of restaurants nearby, and a short drive to fowntown dining and shops. Karl was an excellent host, griendly and very responsive. Would definitely stay here again!"
United States
Ryan
The price is ￥18,656
￥46,118 total
includes taxes & fees
Oct 21 - Oct 22
Fully Furnished 1BR Apartment
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

8. 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, (16 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is ￥18,656
￥46,118 total
includes taxes & fees
Oct 28 - Oct 29
Once the old Schools house now a newly furnished Apartment
A modern kitchen with white cabinets, a stainless steel refrigerator, a dining area with two chairs, and a coffee machine.

9. “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.
“3BR Home Near Wesleyan & Downtown Middletown
A living room with a sofa, a coffee table, and a kitchen area with a brick wall and white appliances.

10. All New Private and Cozy in great location

All New Private and Cozy in great location
Wallingford
8.8 out of 10, Excellent, (6 reviews)
"The pictures must have been old. Very deceiving. Expected it to be more spacious. Hard to get in and out because of the busy road"
United States
ROBERT P.
The price is ￥18,656
￥46,118 total
includes taxes & fees
Oct 18 - Oct 19
All New Private and Cozy in great location
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.

11. 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.
The price is ￥18,656
￥46,118 total
includes taxes & fees
Oct 28 - Oct 29
Newly Remodeled with deck. Close to town center
A compact kitchen with grey cabinets, a built-in microwave, a coffee machine, and a sink with a modern faucet.

12. All New Fully Furnished Cozy Studio

All New Fully Furnished Cozy Studio
Wallingford Center
9.8 out of 10, Exceptional, (9 reviews)
"Clean and well designed apartment in a great location. Book here if you are interested as you won't have any regrets. Enjoy! "
United States
Rick C.
The price is ￥18,656
￥46,118 total
includes taxes & fees
Oct 18 - Oct 19
All New Fully Furnished Cozy Studio
Stairwell

13. 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 ￥18,330
￥43,676 total
includes taxes & fees
Nov 3 - Nov 4
Private Apartment in Berlin
A two-story house with a front porch, a garage, and a well-maintained lawn.

14. 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.
The price is ￥64,851
￥119,654 total
includes taxes & fees
Oct 19 - Oct 20
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
A modern living room with a sofa, a dining table, and a massage chair.

15. #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.
The price is ￥28,507
￥71,656 total
includes taxes & fees
Oct 19 - Oct 20
#29 - Modern 5 Bedroom/2 Bath
A bedroom with a bed, a nightstand, a lamp, and a wooden wardrobe.

16. The Cottage by the Woods -private getaway to relax

The Cottage by the Woods -private getaway to relax
Meriden
The price is ￥42,665
￥100,540 total
includes taxes & fees
Oct 18 - Oct 19
The Cottage by the Woods -private getaway to relax
Building

17. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (12 reviews)
"Bigger than expected! Very nice and lovely little amenities provided."
United States
Hannah Z.
The price is ￥18,656
￥46,118 total
includes taxes & fees
Oct 30 - Oct 31
All New 1BR with tons of Charm
A modern kitchen with a central island, bar stools, and pendant lighting.

18. 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
10.0 out of 10, Exceptional, (34 reviews)
"This was an amazing home that exceeded our expectations- it was clean, comfortable, and in such a beautiful setting! A great place for our family to stay together during a college graduation trip! We would certainly come back again!"
United States
Iris F.
The price is ￥102,713
￥173,585 total
includes taxes & fees
Oct 18 - Oct 19
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

19. 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, (3 reviews)
"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 ￥39,394
￥114,809 total
includes taxes & fees
Oct 28 - Oct 29
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
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

Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

10/10 Excellent
"The staff was delightful. The room was. Clean and comfortable. The complimentary breakfast was very good. Lots of choices to choose from. I would definitely recommend this place to stay. Very convenient to the highway."
Anne 1-night trip
Posted 2 hours ago
Hampton Inn & Suites Hartford/East Hartford

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:

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

Frequently asked questions

Can I find a vacation rental in Middlefield?

Yes, there are vacation rentals in Middlefield close to Lyman Orchards Corn Maze, or you can select a more remote option if you're looking for extra privacy while you relax. 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 vacation rentals in Middlefield?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This vacation home rental outside of Middlefield is located on the beach and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Middlefield?

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

What’s there to see and do in Middlefield?

Lake Beseck Beach and Beseck Lake 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 vacation rental in Middlefield like?

A vacation rental is a private property you can book for a couple of days or more in Middlefield. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for family trips or small group gatherings.