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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Middlefield vacation rentals

Exterior

1. 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 AED 2,053
AED 3,486 total
includes taxes & fees
17 Aug - 18 Aug
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
View from property

2. 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, (175 reviews)
"Beautiful view, very clean !"
United States
Karolyne
The price is AED 584
AED 1,010 total
includes taxes & fees
9 Aug - 10 Aug
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Property grounds

3. #24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"It was great "
United States
Rodrigo C.
The price is AED 782
AED 1,513 total
includes taxes & fees
30 Aug - 31 Aug
#24 *Serenity* A Lakefront Cottage Retreat
Interior

4. 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
9.8 out of 10, Exceptional, (30 reviews)
"Wonderful house in a great location."
United States
Edward S.
The price is AED 2,387
AED 3,798 total
includes taxes & fees
13 Aug - 14 Aug
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Dining

5. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (4 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is AED 474
AED 1,065 total
includes taxes & fees
9 Aug - 10 Aug
2BR Apartment Near Wesleyan 102
TV

6. 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 AED 433
AED 1,071 total
includes taxes & fees
13 Aug - 14 Aug
Newly Remodeled 1-BR Close to Everything yet Very Private
TV

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 AED 433
AED 1,068 total
includes taxes & fees
6 Sep - 7 Sep
Newly Remodeled with deck. Close to town center
Smart TV

8. #29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.4 out of 10, Exceptional, (6 reviews)
"Great place! "
United States
Gail R.
The price is AED 1,136
AED 2,191 total
includes taxes & fees
19 Aug - 20 Aug
#29 - Modern 5 Bedroom/2 Bath
Coffee/tea maker, fridge, microwave, oven

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.
The price is AED 918
AED 1,170 total
includes taxes & fees
31 Aug - 1 Sep
“3BR Home Near Wesleyan & Downtown Middletown
1 bedroom, iron/ironing board, WiFi, bed sheets

10. 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 AED 433
AED 1,071 total
includes taxes & fees
13 Aug - 14 Aug
Once the old Schools house now a newly furnished Apartment
Smart TV, fireplace, books, music library

11. 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, (34 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 AED 459
AED 940 total
includes taxes & fees
31 Aug - 1 Sep
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Exterior

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, (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 1,071 total
includes taxes & fees
26 Aug - 27 Aug
All New Studio apartment in center of town
Exterior

13. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is AED 433
AED 1,071 total
includes taxes & fees
11 Aug - 12 Aug
All New 1BR with tons of Charm
TV

14. 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 1,071 total
includes taxes & fees
12 Aug - 13 Aug
All New Private and Cozy in great location
Coffee/tea maker, fridge, microwave, oven

15. #16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Southington
9.0 out of 10, Wonderful, (8 reviews)
"We enjoyed our stay! And happy with most!!!!"
United States
Dawn H.
The price is AED 900
AED 1,876 total
includes taxes & fees
9 Aug - 10 Aug
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Interior

16. Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.0 out of 10, Wonderful, (7 reviews)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
The price is AED 448
AED 1,044 total
includes taxes & fees
9 Aug - 10 Aug
Private Apartment in Berlin
Smart TV

17. #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 1,175
AED 2,060 total
includes taxes & fees
29 Aug - 30 Aug
#23 *COMFORT & LUXURY* 3 BR/2 BA House
Property grounds

18. 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 AED 529
AED 1,156 total
includes taxes & fees
17 Aug - 18 Aug
Lakeview Carriage House with Spectacular Sunset Views
Interior

19. #11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10

#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10
Plainville
10.0 out of 10, Exceptional, (3 reviews)
"Great weekend with friends!"
United States
Neil R.
#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10
TV, fireplace

20. #41- Available 12/8! - sleeps 14

#41- Available 12/8! - sleeps 14
Southington
#41- Available 12/8! - sleeps 14
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
"Best front staff ever! So friendly and kind and very clean property. Love the downstairs convenience store and the wine station after a long day. Would definitely stay again."
Andrea 1-night trip
Posted 6 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?

Cozy 1-bedroom house in lovely New Haven with AC close to Yale University: This vacation home rental outside of Middlefield is equipped with a patio, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

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 Wadsworth Falls State Park 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.