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

Middlefield Holiday Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Middlefield holiday rentals

View from property

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.6 out of 10, Exceptional, (160 reviews)
"Great stay! "
United States
Tanitra
The price is HK$1,325
HK$1,885 total
includes taxes & fees
1 Jul - 2 Jul
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
1 bedroom, desk, iron/ironing board, travel cot

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (46 reviews)
"We enjoyed our stay"
United States
JM B.
The price is HK$1,348
HK$2,341 total
includes taxes & fees
27 Jul - 28 Jul
1-bedroom cottage with Grove Beach 🏖️ access.
Living area

The Beach Nest-Lux Cottage Steps to the Beach

The Beach Nest-Lux Cottage Steps to the Beach
Clinton
9.8 out of 10, Exceptional, (6 reviews)
"This is exactly what we needed. Nice area, great place to walk, easy to relax. "
United States
Karol W.
The Beach Nest-Lux Cottage Steps to the Beach
Dining

Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (76 reviews)
"Spacious"
United States
Mehul
The price is HK$1,019
HK$1,804 total
includes taxes & fees
30 Jun - 1 Jul
Spacious 2 Bedroom apartment close to Yale Bowl
Property grounds

Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (4 reviews)
"the place was clean bed was nice"
United States
Jonathan
The price is HK$941
HK$1,239 total
includes taxes & fees
30 Jun - 1 Jul
Humble Abode #2
TV

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 HK$925
HK$2,264 total
includes taxes & fees
28 Jul - 29 Jul
Newly Remodeled with deck. Close to town center
Fridge, microwave, oven, stovetop

The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
10.0 out of 10, Exceptional, (24 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is HK$2,470
HK$3,933 total
includes taxes & fees
1 Jul - 2 Jul
The gardners Cottage 1 mile from long Island Sound - pet friendly
Exterior

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (38 reviews)
"Needed a one night stay - worked fine"
United States
Michelle B.
The price is HK$1,529
HK$2,460 total
includes taxes & fees
3 Jul - 4 Jul
Walk To Goodspeed Opera House!
Property grounds

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Lake Pocotopaug
10.0 out of 10, Exceptional, (16 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is HK$1,396
HK$2,750 total
includes taxes & fees
23 Jul - 24 Jul
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Smart TV, fireplace, books, music library

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, (33 reviews)
"Fantastic experience from beginning to end! Loved every minute of my stay! "
United States
Jody U.
The price is HK$1,215
HK$2,325 total
includes taxes & fees
7 Jul - 8 Jul
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Fridge, microwave, oven, stovetop

#26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home
Plainville
10.0 out of 10, Exceptional, (5 reviews)
"Lovely home and a great experience. Highly highly highly recommend!! "
United States
Hector D.
The price is HK$1,502
HK$2,629 total
includes taxes & fees
3 Jul - 4 Jul
#26 Beautifully Renovated 2 BR Home
Dining

1 Min to I-91 - Newly Renovated Modern 2 BR Home

1 Min to I-91 - Newly Renovated Modern 2 BR Home
Berlin
The price is HK$1,477
HK$2,796 total
includes taxes & fees
7 Jul - 8 Jul
1 Min to I-91 - Newly Renovated Modern 2 BR Home
Exterior

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 HK$925
HK$2,287 total
includes taxes & fees
5 Jul - 6 Jul
All New 1BR with tons of Charm
Exterior

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
The price is HK$1,023
HK$2,516 total
includes taxes & fees
30 Jun - 1 Jul
Angelica’s safe haven @ west haven
1 bedroom, iron/ironing board, WiFi, bed sheets

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, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is HK$925
HK$2,287 total
includes taxes & fees
5 Jul - 6 Jul
Once the old Schools house now a newly furnished Apartment
Exterior

Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.0 out of 10, Wonderful, (14 reviews)
"Conveniently located and nice, practically appointed stay for a business trip to work with a collaborator in town."
United States
Jeremy Y.
The price is HK$847
HK$1,910 total
includes taxes & fees
1 Jul - 2 Jul
Bright Downtown Studio near Yale & East Rock!
TV

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 HK$925
HK$2,311 total
includes taxes & fees
11 Jul - 12 Jul
Newly Remodeled 1-BR Close to Everything yet Very Private
Terrace/patio

The Blue Back Bungalow

The Blue Back Bungalow
West Hartford
9.4 out of 10, Exceptional, (18 reviews)
"Great location and pleasant area to walk to area restaurants and shops. Prompt and friendly communication with host who was very accommodating to our needs. We enjoyed our stay."
United States
Laurie R.
The price is HK$855
HK$2,747 total
includes taxes & fees
19 Jul - 20 Jul
The Blue Back Bungalow
1 bedroom, iron/ironing board, WiFi, bed sheets

Cozy 1-bedroom house in lovely New Haven with AC close to YaleUniversity

Cozy 1-bedroom house in lovely New Haven with AC close to YaleUniversity
Fair Haven
The price is HK$635
HK$887 total
includes taxes & fees
13 Jul - 14 Jul
Cozy 1-bedroom house in lovely New Haven with AC close to YaleUniversity
TV

Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.

Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.
Dwight
8.0 out of 10, Very good, (2 reviews)
"The studio apartment is in a very convenient location. It is a lovely walk to Yale. Many restaurants just outside the door. My friends, who joined me for a meal, found parking easily. It was a plus having use of a parking pass for Dwight Street. We never had a problem getting a parking spot. We also loved being able to bring our two small pups with us. The bottle of wine was a thoughtful touch. "
United States
ELIZABETH M S M.
The price is HK$1,078
HK$1,837 total
includes taxes & fees
13 Jul - 14 Jul
Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.
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

Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"Very nice throwback hotel with beautiful grounds and large rooms."
David 2-night trip
Posted 1 hour ago
Avon Old Farms Hotel

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:

  • View our selection of featured holiday rentals in Middlefield
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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 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?

Amazing Lakefront Property: This highly rated holiday home rental in Middlefield is located on a lake, and has a fireplace, a balcony and a BBQ 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. Make the most of garden in this rental home to help you unwind.

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 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 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.