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

Holiday Rentals in Middlefield

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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 holiday 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.
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
8.8 out of 10, Excellent, (8 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is €212
includes taxes & fees
12 Nov - 13 Nov
2BR Apartment Near Wesleyan 102
Veterans Park, near the house

3. 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 €223
includes taxes & fees
16 Nov - 17 Nov
Family Stays: Middletown, CT
A cabin with a dining table set for two, a bicycle, and a small porch area.

4. 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, (222 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
The price is €172
includes taxes & fees
10 Dec - 11 Dec
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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.

5. 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.
The price is €228
includes taxes & fees
17 Nov - 18 Nov
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A kitchen with dark cabinets, a granite countertop, a black stove, a microwave, and a sink.

6. 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 €260
includes taxes & fees
25 Nov - 26 Nov
Fully Furnished 1BR Apartment
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.

7. 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 €261
includes taxes & fees
16 Nov - 17 Nov
Newly Remodeled with deck. Close to town center
A living room with a blue sofa, patterned armchair, wooden coffee table, and a globe on a side table.

8. 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.
The price is €276
includes taxes & fees
14 Nov - 15 Nov
Brand New Platform #1
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

9. 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 €257
includes taxes & fees
12 Nov - 13 Nov
Once the old Schools house now a newly furnished Apartment
A modern kitchen with a wooden island, white cabinetry, and a ceiling fan.

10. 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.
New Railside Residents
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

11. 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 €260
includes taxes & fees
19 Nov - 20 Nov
All New Studio apartment in center of town
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

12. 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 €421
includes taxes & fees
23 Nov - 24 Nov
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Stairwell

13. 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 €223
includes taxes & fees
12 Nov - 13 Nov
Private Apartment in Berlin
A hotel reception area with a receptionist, a guest, and a child.

14. 1 Queen Bed | Wethersfield

1 Queen Bed | Wethersfield
Wethersfield
10.0 out of 10, Exceptional, (47 reviews)
"Quick check-in and quiet room helped us get good rest before hitting the road again."
United States
Anonymous traveller
The price is €75
includes taxes & fees
12 Nov - 13 Nov
1 Queen Bed | Wethersfield
A modern kitchen with a central island, bar stools, and pendant lighting.

15. 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.
The price is €1,030
includes taxes & fees
12 Nov - 13 Nov
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Building

16. 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 €269
includes taxes & fees
24 Nov - 25 Nov
All New 1BR with tons of Charm
A hotel room with a neatly made bed, a bedside table with a lamp, and a window with patterned curtains.

17. 2 Full Beds | Wethersfield

2 Full Beds | Wethersfield
Wethersfield
10.0 out of 10, Exceptional, (52 reviews)
"My short stopover went well, beds were supportive but not too firm, setting remained calm despite being next to interstate."
United States
Anonymous traveller
The price is €80
includes taxes & fees
12 Nov - 13 Nov
2 Full Beds | Wethersfield
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.
The price is €261
includes taxes & fees
16 Nov - 17 Nov
All New Fully Furnished Cozy Studio
A wooden desk with a black office chair, a window with a view of trees, and a box labeled "Circuit Maze" on top.

19. 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 €179
includes taxes & fees
7 Dec - 8 Dec
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
A large, white, multi-story building with a prominent tower and a flag on top.

20. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (43 reviews)
"Very convenient location with good parking"
United States
Anonymous traveller
The price is €273
includes taxes & fees
24 Nov - 25 Nov
Walk To Goodspeed Opera House!
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

Economy Inn

Economy Inn

8/10 Good
"I am not sure but it seems like this hotel has new management. If not, then the old owners finally gave the place a makeover."
Joseph 1-night trip
Posted 8 hours ago
Economy Inn

Find out more about Middlefield

Everything you need to know about Middlefield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlefield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 Middlefield holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middlefield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlefield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlefield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlefield holiday rentals we have selected for you start as low as €172 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middlefield rentals

At Expedia, we put the best Middlefield holiday 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 Middlefield 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 Middlefield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlefield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Middlefield?

Yes, there are holiday rentals in Middlefield close to Lyman Orchards Corn Maze, 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?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This holiday home rental outside of Middlefield is located on the beach, and has a balcony, a BBQ 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 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 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 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.