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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Middlefield vacation rentals

Exterior

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, (194 reviews)
"ABSOLUTELY BEAUTIFUL AND SERENE STAY . WE REALLY ENJOYED OUR STAY !"
United States
Melissa
The price is AED 496
AED 740 total
includes taxes & fees
5 Oct - 6 Oct
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Property grounds

2. #24 Serenity A Lakefront Cottage Retreat

#24 Serenity A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (25 reviews)
"It was great "
United States
Rodrigo C.
The price is AED 566
AED 1,183 total
includes taxes & fees
29 Sep - 30 Sep
#24 Serenity A Lakefront Cottage Retreat
Exterior

3. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (31 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
The price is AED 514
AED 939 total
includes taxes & fees
27 Oct - 28 Oct
Family Stays: Middletown, CT
Coffee/tea maker, fridge, microwave, oven

4. 2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
10.0 out of 10, Exceptional, (3 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 AED 411
AED 1,053 total
includes taxes & fees
30 Sep - 1 Oct
2BR Apartment Near Wesleyan 301
Smart TV, fireplace, books, music library

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, (37 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 AED 459
AED 918 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Dining

6. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (6 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is AED 450
AED 1,004 total
includes taxes & fees
29 Sep - 30 Sep
2BR Apartment Near Wesleyan 102
Interior

7. 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 AED 337
AED 884 total
includes taxes & fees
29 Sep - 30 Sep
Private Apartment in Berlin
1 bedroom, iron/ironing board, WiFi, bed sheets

8. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.2 out of 10, Wonderful, (15 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is AED 433
AED 1,031 total
includes taxes & fees
29 Sep - 30 Sep
Once the old Schools house now a newly furnished Apartment
Exterior

9. 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 AED 1,689
AED 2,858 total
includes taxes & fees
29 Sep - 30 Sep
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Coffee/tea maker, fridge, microwave, oven

10. 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 AED 433
AED 1,031 total
includes taxes & fees
5 Oct - 6 Oct
All New Fully Furnished Cozy Studio
Iron/ironing board, WiFi, bed sheets

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

The Cottage by the Woods -private getaway to relax
Meriden
The price is AED 992
AED 2,223 total
includes taxes & fees
29 Sep - 30 Sep
The Cottage by the Woods -private getaway to relax
TV

12. 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)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
The price is AED 433
AED 1,031 total
includes taxes & fees
5 Oct - 6 Oct
Newly Remodeled 1-BR Close to Everything yet Very Private
Interior

13. 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, (32 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 AED 2,387
AED 3,585 total
includes taxes & fees
1 Oct - 2 Oct
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
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 AED 433
AED 1,031 total
includes taxes & fees
29 Sep - 30 Sep
All New Studio apartment in center of town
TV

15. 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 AED 433
AED 1,031 total
includes taxes & fees
30 Sep - 1 Oct
All New Private and Cozy in great location
Smart TV

16. #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 AED 804
AED 1,758 total
includes taxes & fees
7 Oct - 8 Oct
#29 - Modern 5 Bedroom/2 Bath
Smart TV

17. 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, (24 reviews)
"Great place clean and quiet "
United States
James P.
The price is AED 443
AED 752 total
includes taxes & fees
29 Sep - 30 Sep
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Apartment (1 Bedroom) | Interior

18. Bristol Condo Near Espn HQ & Lake Compounce!

Bristol Condo Near Espn HQ & Lake Compounce!
3.5 star property
Bristol
The price is AED 643
AED 1,153 total
includes taxes & fees
2 Oct - 3 Oct
Bristol Condo Near Espn HQ & Lake Compounce!
Smart TV

19. #23 COMFORT & LUXURY 3 BR/2 BA House

#23 COMFORT & LUXURY 3 BR/2 BA House
Southington
9.8 out of 10, Exceptional, (9 reviews)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
The price is AED 582
AED 1,238 total
includes taxes & fees
7 Oct - 8 Oct
#23 COMFORT & LUXURY 3 BR/2 BA House
Exterior

20. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Bigger than expected! Very nice and lovely little amenities provided."
United States
Hannah Z.
The price is AED 433
AED 1,031 total
includes taxes & fees
12 Oct - 13 Oct
All New 1BR with tons of Charm
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
"Really nice hotel. Easy check in and out."
Leslie 1-night trip
Posted 3 hours ago
New Haven Hotel

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.