Photo by Chris Kailher

Middlefield Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
15 Aug - 16 Aug
Tomorrow
16 Aug - 17 Aug
This weekend
15 Aug - 17 Aug
Next weekend
22 Aug - 24 Aug

Holiday Rentals in Middlefield

Postcard Cabins Machimoodus
Exterior

Postcard Cabins Machimoodus

2.0 star property
9.6 out of 10, Exceptional, (47)
"Great stay"
The price is HK$1,166
HK$1,656 total
includes taxes & fees
17 Aug - 18 Aug
Postcard Cabins Machimoodus
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎
Exterior

COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

10.0 out of 10, Exceptional, (40)
"My wife and I loved our weekend stay at this cabin!"
The price is HK$2,644
HK$5,242 total
includes taxes & fees
26 Aug - 27 Aug
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (28)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is HK$1,121
HK$2,104 total
includes taxes & fees
27 Aug - 28 Aug
1-bedroom cottage with Grove Beach 🏖️ access.
Shoreline Oasis
Exterior

Shoreline Oasis

9.0 out of 10, Wonderful, (6)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is HK$1,401
HK$2,055 total
includes taxes & fees
14 Sept - 15 Sept
Shoreline Oasis
Waterfront Goodspeed airport 2-bedroom house with AC, WiFi
Sun-loungers, beach towels

Waterfront Goodspeed airport 2-bedroom house with AC, WiFi

2.0 star property
9.2 out of 10, Wonderful, (10)
"Beautiful location, very comfortable for our small family."
Waterfront Goodspeed airport 2-bedroom house with AC, WiFi
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Outdoor pool, a heated pool

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (138)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
Dining

Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

9.8 out of 10, Exceptional, (66)
"We very much enjoyed our stay and were pleasantly surprised by how great the views were from practically every room in the house. Check-in was very simple and there were many nice touches awaiting us at the property. "
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
Cozy 3 bedroom minutes from Yale and the beach
Private kitchen

Cozy 3 bedroom minutes from Yale and the beach

7.4 out of 10, Good, (3)
"The inside was very clean, the back patio/garden area is cute, but the pool was green by day two. Overall we enjoyed our time here"
Cozy 3 bedroom minutes from Yale and the beach
Totally Private Cozy studio in awesome Hartford with WiFi, AC
WiFi, bed sheets

Totally Private Cozy studio in awesome Hartford with WiFi, AC

9.4 out of 10, Exceptional, (8)
"I was a little worried to be right in downtown with just me and my daughter. But this location was very safe and cute shopping area around the apartment. "
The price is HK$854
HK$1,274 total
includes taxes & fees
31 Aug - 1 Sept
Totally Private Cozy studio in awesome Hartford with WiFi, AC
Cozy 1-bedroom apartment in cool New Haven with WiFi, fitness room
Games room

Cozy 1-bedroom apartment in cool New Haven with WiFi, fitness room

The price is HK$1,197
HK$2,362 total
includes taxes & fees
29 Aug - 30 Aug
Cozy 1-bedroom apartment in cool New Haven with WiFi, fitness room
Cozy apartment in charming Hartford with AC, WiFi
Microwave

Cozy apartment in charming Hartford with AC, WiFi

10.0 out of 10, Exceptional, (2)
"Owner didn’t respond to messages and there was issues with the virtual key QR code However after check in everything was wonderful and I had no issues "
The price is HK$900
HK$1,326 total
includes taxes & fees
14 Sept - 15 Sept
Cozy apartment in charming Hartford with AC, WiFi
Luxury Furnished Apartments by Hyatus Downtown at Yale
In-room dining

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.6 out of 10, Exceptional, (52)
"Great location, great stay!"
Luxury Furnished Apartments by Hyatus Downtown at Yale
Luxury Apartments by Hyatus at Pierpont
Seasonal outdoor pool

Luxury Apartments by Hyatus at Pierpont

4.0 star property
9.4 out of 10, Exceptional, (19)
"Excellent location downtown and close to yale. A lot of complimentary amenities and activities. Very nice size rooms. A nice residential feel for a weeks stay."
Luxury Apartments by Hyatus at Pierpont
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Terrace/patio

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
The Beach Nest-Lux Cottage Steps to the Beach
Living area

The Beach Nest-Lux Cottage Steps to the Beach

9.8 out of 10, Exceptional, (6)
"Quick weekend stay as we needed to be in the area for a soccer tournament. The house was super clean and had everything we needed. Would definitely stay again. "
The Beach Nest-Lux Cottage Steps to the Beach
Waterfront Estate Home - Beach and Shared Pool - East
Dining

Waterfront Estate Home - Beach and Shared Pool - East

9.8 out of 10, Exceptional, (43)
"Perfect home for a big family gathering!"
Waterfront Estate Home - Beach and Shared Pool - East
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Property grounds

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (35)
"Clean stunning views amazing host "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Beachside Branford- walk to Beach, Grill
Dining

Beachside Branford- walk to Beach, Grill

9.8 out of 10, Exceptional, (6)
"Charming little cottage that was just right for our trip to the CT shoreline."
Beachside Branford- walk to Beach, Grill
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Smart TV, fireplace, video games

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

10.0 out of 10, Exceptional, (18)
"I've stayed here multiple times and it was amazing as always. Great communication, clean, and beautiful! "
The price is HK$3,772
HK$6,395 total
includes taxes & fees
18 Aug - 19 Aug
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
New Madison beach house - Ocean front- Great views- booking Summer 2025
Exterior

New Madison beach house - Ocean front- Great views- booking Summer 2025

10.0 out of 10, Exceptional, (65)
"Great location "
New Madison beach house - Ocean front- Great views- booking Summer 2025
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlefield Hotel Reviews

New Haven Hotel

New Haven Hotel

10/10 Excellent
"Great hotel"
tim 1-night trip
Posted 1 day ago
New Haven Hotel

Frequently asked questions

Can I find a holiday rental in Middlefield?

Yes, there are holiday rentals close to the most popular sights in Middlefield, 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?

Waterfront Goodspeed airport 2-bedroom house with AC, WiFi: This holiday home rental outside of Middlefield is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.