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
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Middlefield vacation rentals

Veterans Park, near the house

1. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (34 reviews)
"Gilbert is an amazing host! I highly recommend staying here if you are visiting Middletown."
United States
Audrey F.
The price is AED 496
AED 925 total
includes taxes & fees
16 Nov - 17 Nov
Family Stays: Middletown, CT
A compact kitchen with stainless steel appliances, a marble countertop, and a black coffee maker.

2. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
8.8 out of 10, Excellent, (8 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is AED 400
AED 933 total
includes taxes & fees
14 Nov - 15 Nov
2BR Apartment Near Wesleyan 102
A two-story house with a front porch, large windows, and a well-maintained lawn.

3. 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, (35 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.
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
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.

4. 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, (40 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.
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A cabin surrounded by a natural forest setting with a fire pit and picnic table.

5. 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, (223 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
The price is AED 466
AED 705 total
includes taxes & fees
14 Dec - 15 Dec
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A modern kitchen with a wooden island, white cabinetry, and a ceiling fan.

6. New Railside Residents

New Railside Residents
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"Clean & comfortable, in an architecturally unique setting. Great proximity to a variety of downtown shops & restaurants - check out Center Street Brewing Co. for some excellent beer."
United States
Thomas S.
The price is AED 485
AED 1,094 total
includes taxes & fees
16 Nov - 17 Nov
New Railside Residents
A living room with a blue sofa, patterned armchair, wooden coffee table, and a globe on a side table.

7. Brand New Platform #1

Brand New Platform #1
Wallingford Center
9.6 out of 10, Exceptional, (4 reviews)
"This is the second time we have stayed at this location, although it was a different "platform/room." Once again, a very nice stay. Room was perfect for the 2 of us, and all the right ameneties. This is a perfect location within Wallenford, with access to everything, whether walking or driving. The property is very well maintained, and feels very secure. "
United States
Cherie G.
Brand New Platform #1
A kitchen with a wooden island, white appliances, and a window with curtains.

8. 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 AED 485
AED 1,094 total
includes taxes & fees
16 Nov - 17 Nov
Newly Remodeled with deck. Close to town center
A kitchen with dark cabinets, a black refrigerator, a microwave, and a granite countertop island.

9. 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
Fully Furnished 1BR Apartment
Kitchen

10. Private Apartment in Berlin

Private Apartment in Berlin
Berlin
8.8 out of 10, Excellent, (8 reviews)
"Clean, convenient, and great location."
United States
Shaun L.
The price is AED 441
AED 992 total
includes taxes & fees
16 Nov - 17 Nov
Private Apartment in Berlin
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

11. 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, (11 reviews)
"We really liked this property! Modernized apartment in an older home. Clean, comfortable, and close to family in the area. Karl was great to work with. We will stay here again next time we visit family!"
United States
Alan
The price is AED 485
AED 1,057 total
includes taxes & fees
9 Dec - 10 Dec
Newly Remodeled 1-BR Close to Everything yet Very Private
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

12. 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.
All New Studio apartment in center of town
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

13. 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 AED 485
AED 1,094 total
includes taxes & fees
16 Nov - 17 Nov
Once the old Schools house now a newly furnished Apartment
A living room with a brick fireplace, white furniture, and a patterned rug.

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

The Cottage by the Woods -private getaway to relax
Meriden
The price is AED 1,102
AED 2,383 total
includes taxes & fees
14 Nov - 15 Nov
The Cottage by the Woods -private getaway to relax
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

15. 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 AED 294
AED 1,715 total
includes taxes & fees
20 Nov - 21 Nov
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
A hotel reception area with a counter, a digital tablet, and a poster on the wall.

16. 1 Queen Bed | Micfridge

1 Queen Bed | Micfridge
Wethersfield
10.0 out of 10, Exceptional, (51 reviews)
"Quick stop, quiet room near the highway."
United States
Anonymous traveler
The price is AED 279
AED 321 total
includes taxes & fees
15 Nov - 16 Nov
1 Queen Bed | Micfridge
A hotel reception area with a receptionist, a guest, and a child.

17. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Wethersfield
10.0 out of 10, Exceptional, (49 reviews)
"Simple rooms close to I-91 made travel convenient."
United States
Anonymous traveler
1 Queen Bed | Smoking
A compact kitchen with grey cabinets, a built-in microwave, a coffee machine, and a sink with a modern faucet.

18. 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.
All New Fully Furnished Cozy Studio
Building

19. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (13 reviews)
"Bigger than expected! Very nice and lovely little amenities provided."
United States
Hannah Z.
The price is AED 485
AED 1,094 total
includes taxes & fees
16 Nov - 17 Nov
All New 1BR with tons of Charm
A wooden porch with a concrete step leading to a door.

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

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.0 out of 10, Wonderful, (26 reviews)
"Great place clean and quiet "
United States
James P.
The price is AED 437
AED 694 total
includes taxes & fees
14 Dec - 15 Dec
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
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

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"Everything was great just make sure you get there before it gets dark out. It’s relevantly hard to find the cabins in the pitch black. Overall the area was very quiet. We had neighbors but you really can’t hear anyone around you. It’s a great way to disconnect and unwind."
Cynthia 2-night trip
Posted 5 hours ago
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

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.