Middlefield Holiday Rentals

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

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
2.0 star property
East Haddam
9.6 out of 10, Exceptional, (145 reviews)
"Great stay! "
United States
Tanitra
The price is HK$1,089
HK$1,613 total
includes taxes & fees
30 Apr - 1 May
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Smart TV, books

Clear LI Sound waterview, Wedding pics, Yale&Beach

Clear LI Sound waterview, Wedding pics, Yale&Beach
East Shore
10.0 out of 10, Exceptional, (11 reviews)
"Great stay! Would definitely stay again! "
United States
Frankie O.
The price is HK$4,506
HK$7,698 total
includes taxes & fees
3 May - 4 May
Clear LI Sound waterview, Wedding pics, Yale&Beach
Interior

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
Oakville
The price is HK$1,920
HK$4,219 total
includes taxes & fees
28 Apr - 29 Apr
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Smart TV

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
9.4 out of 10, Exceptional, (22 reviews)
"Great place"
United States
John S.
The price is HK$1,168
HK$2,494 total
includes taxes & fees
28 Apr - 29 Apr
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Marina

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Fair Haven
9.6 out of 10, Exceptional, (15 reviews)
"A cozy pet and family-friendly property. Very spacious."
United States
Wallace R.
The price is HK$1,410
HK$2,601 total
includes taxes & fees
28 Apr - 29 Apr
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Dining

McAngel Haven: 5 mins from Yale

McAngel Haven: 5 mins from Yale
West Haven
9.6 out of 10, Exceptional, (20 reviews)
"Excellent location Clean and spacious Comfortable beds "
United States
Joseph T.
The price is HK$1,798
HK$4,097 total
includes taxes & fees
28 Apr - 29 Apr
McAngel Haven: 5 mins from Yale
Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (22 reviews)
"The house was cozy and comfortable. The location was great while dropping our son off at Wesleyan University for his sophomore year. The lake was a peaceful place to relax and read."
United States
julia h.
The price is HK$1,668
HK$3,180 total
includes taxes & fees
19 May - 20 May
#24 *Serenity* A Lakefront Cottage Retreat
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$2,514 total
includes taxes & fees
28 Apr - 29 Apr
Angelica’s safe haven @ west haven
Smart TV

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

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.4 out of 10, Exceptional, (18 reviews)
"Easy check in Rooms were comfortably spacious "
United States
Benjamin W.
The price is HK$797
HK$1,434 total
includes taxes & fees
29 Apr - 30 Apr
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Fridge, microwave, oven, stovetop

Heavenly Home in New Haven /5 mins drive from Yale

Heavenly Home in New Haven /5 mins drive from Yale
Fair Haven
9.2 out of 10, Wonderful, (23 reviews)
"This house has everything you need to enjoy a getaway. Clean, It will sleep 20 and their is room for 20 to gather."
United States
Kathy B.
The price is HK$4,611
HK$6,157 total
includes taxes & fees
30 Apr - 1 May
Heavenly Home in New Haven /5 mins drive from Yale
Interior

East Haddam Lake View Rental

East Haddam Lake View Rental
East Haddam
The price is HK$1,559
HK$3,122 total
includes taxes & fees
28 Apr - 29 Apr
East Haddam Lake View Rental
Exterior

Orange Oasis in Heart of East Rock |Free Parking| Near Yale & DT

Orange Oasis in Heart of East Rock |Free Parking| Near Yale & DT
East Rock
8.8 out of 10, Excellent, (9 reviews)
"The pictures need to change "
United States
Dosu
The price is HK$1,277
HK$3,246 total
includes taxes & fees
28 Apr - 29 Apr
Orange Oasis in Heart of East Rock |Free Parking| Near Yale & DT
Exterior

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (36 reviews)
"Place was clean, beds were comfortable. We were only there one night but was well worth it."
United States
Annette L.
The price is HK$1,207
HK$2,058 total
includes taxes & fees
10 May - 11 May
Walk To Goodspeed Opera House!
Interior

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, (26 reviews)
"Wonderful house in a great location."
United States
Edward S.
The price is HK$4,701
HK$7,597 total
includes taxes & fees
28 Apr - 29 Apr
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
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, (30 reviews)
"Fantastic experience from beginning to end! Loved every minute of my stay! "
United States
Jody U.
The price is HK$979
HK$2,006 total
includes taxes & fees
4 May - 5 May
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
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$2,286 total
includes taxes & fees
1 May - 2 May
Once the old Schools house now a newly furnished Apartment
Interior

Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches
East Shore
8.8 out of 10, Excellent, (3 reviews)
"Fantastic place, amazing hosts, 100% recommend! "
United States
Zach P.
The price is HK$2,010
HK$3,972 total
includes taxes & fees
29 Apr - 30 Apr
Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches
Exterior

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
9.8 out of 10, Exceptional, (8 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is HK$925
HK$2,286 total
includes taxes & fees
1 May - 2 May
All New 1BR with tons of Charm
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, (40 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is HK$628
HK$1,410 total
includes taxes & fees
28 Apr - 29 Apr
1-bedroom cottage with Grove Beach 🏖️ access.
1 bedroom, desk, iron/ironing board, WiFi

One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
The price is HK$729
HK$1,580 total
includes taxes & fees
28 Apr - 29 Apr
One bedroom in United States of America, New Haven
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

Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton

10/10 Excellent
"amazing service and clean room"
Tapasya 2-night trip
Posted 2 hours ago
Hotel Marcel New Haven, Tapestry Collection By Hilton

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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  • Enter your travel dates to view the best deals on holiday rentals in Middlefield while they last

Look no further and take a look at our great range of rental properties in Middlefield!

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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?

Oceanfront Getaway - Quiet, Firepit + Pvt Beach: This holiday home rental outside of Middlefield is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 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 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.