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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Middlefield vacation rentals

View from property

1. 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, (184 reviews)
"Beautiful cabin! Will def go again!"
United States
Morainny
The price is ￥20,275
￥38,045 total
includes taxes & fees
Sep 3 - Sep 4
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Exterior

2. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Very nice! Clean and had everything you would need for a few nights away from home. I book again. "
United States
ALRUNDUS L.
The price is ￥18,891
￥47,339 total
includes taxes & fees
Aug 31 - Sep 1
All New 1BR with tons of Charm
Smart TV, fireplace, books, music library

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, (36 reviews)
"My son and I were here for two nights and had an excellent time. It was exactly as described and such a tastefully decorated and maintained place to stay. Would definitely stay here again if in the area!"
United States
Kate F.
The price is ￥20,011
￥41,463 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
TV

4. 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, (10 reviews)
"Best stay ever! Parking lot was easy; apartment was clean and felt like home. Bed comfortable. Would booked this apartment next trip. My only recommendation that was the kitchen did not have a toaster. "
United States
Linda v.
The price is ￥18,891
￥47,339 total
includes taxes & fees
Sep 20 - Sep 21
Newly Remodeled 1-BR Close to Everything yet Very Private
TV

5. 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 ￥18,891
￥47,339 total
includes taxes & fees
Sep 10 - Sep 11
Newly Remodeled with deck. Close to town center
1 bedroom, iron/ironing board, WiFi, bed sheets

6. 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, (14 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is ￥18,891
￥47,339 total
includes taxes & fees
Aug 31 - Sep 1
Once the old Schools house now a newly furnished Apartment
TV

7. All new 1BR apartment with all the features you are looking for

All new 1BR apartment with all the features you are looking for
Wallingford Center
10.0 out of 10, Exceptional, (1 review)
"Clean & Comfortable, excellent accessibility to area restaurants & shopping.There was a hitch with my payment before check-in, the owner was helpful & communicative in resolving the issue.Overall, a great place to stay."
United States
Thomas S.
The price is ￥18,891
￥47,339 total
includes taxes & fees
Aug 31 - Sep 1
All new 1BR apartment with all the features you are looking for
Interior

8. 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 ￥14,696
￥39,633 total
includes taxes & fees
Aug 31 - Sep 1
Private Apartment in Berlin
Coffee/tea maker, fridge, microwave, oven

9. All New Fully Furnished Cozy Studio

All New Fully Furnished Cozy Studio
Wallingford Center
9.8 out of 10, Exceptional, (8 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 ￥18,891
￥47,339 total
includes taxes & fees
Sep 12 - Sep 13
All New Fully Furnished Cozy Studio
Smart TV

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

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
8.8 out of 10, Excellent, (23 reviews)
"Great place clean and quiet "
United States
James P.
The price is ￥18,875
￥32,753 total
includes taxes & fees
Sep 1 - Sep 2
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Coffee/tea maker, fridge, microwave, oven

11. “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.
The price is ￥36,020
￥46,386 total
includes taxes & fees
Aug 31 - Sep 1
“3BR Home Near Wesleyan & Downtown Middletown
Iron/ironing board, WiFi, bed sheets

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

The Cottage by the Woods -private getaway to relax
Meriden
The price is ￥43,224
￥102,497 total
includes taxes & fees
Sep 12 - Sep 13
The Cottage by the Woods -private getaway to relax
TV

13. Old Silver factory converted to a new 1Br with all the charm

Old Silver factory converted to a new 1Br with all the charm
Wallingford Center
The price is ￥18,891
￥47,179 total
includes taxes & fees
Sep 26 - Sep 27
Old Silver factory converted to a new 1Br with all the charm
Exterior

14. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."
United States
Nadine C.
The price is ￥18,891
￥47,339 total
includes taxes & fees
Aug 31 - Sep 1
All New Studio apartment in center of town
Property grounds

15. Lakeview Carriage House with Spectacular Sunset Views

Lakeview Carriage House with Spectacular Sunset Views
Lake Pocotopaug
10.0 out of 10, Exceptional, (19 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is ￥23,053
￥50,524 total
includes taxes & fees
Sep 7 - Sep 8
Lakeview Carriage House with Spectacular Sunset Views
Interior

16. The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
9.0 out of 10, Wonderful, (26 reviews)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
The price is ￥11,046
￥40,459 total
includes taxes & fees
Aug 31 - Sep 1
The Sun Filled Cozy Creamery
TV

17. 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 ￥18,891
￥47,339 total
includes taxes & fees
Sep 21 - Sep 22
Brand New Platform #1
Exterior

18. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (40 reviews)
"Simple process, plenty of room, ample parking and no issues with noise from the business above. "
United States
Amber J.
The price is ￥23,373
￥40,567 total
includes taxes & fees
Sep 22 - Sep 23
Walk To Goodspeed Opera House!
Exterior

19. 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
9.8 out of 10, Exceptional, (17 reviews)
"Large, comfortable house in a tranquil part of town. "
United States
Daryl R.
The price is ￥81,838
￥142,021 total
includes taxes & fees
Sep 8 - Sep 9
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Apartment (1 Bedroom) | Interior

20. Bristol Condo Near Espn HQ & Lake Compounce!

Bristol Condo Near Espn HQ & Lake Compounce!
3.5 star property
Bristol
The price is ￥23,373
￥44,895 total
includes taxes & fees
Sep 1 - Sep 2
Bristol Condo Near Espn HQ & Lake Compounce!
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

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

10/10 Excellent
"Check in was easy and quick. The person checking is in was nice and friendly. The rooms are modern spacious and clean. The lobby is very large and comfortable with a lot of seating. Overall, really nice place easy location to get to. There is a fee for parking, which is an additional $26 per day I believe. So that can easily add up if you have a lengthy stay."
Alma 2-night trip
Posted 5 hours ago
Cambria Hotel New Haven University Area

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.