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

Search Holiday Homes in Middlefield

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Middlefield holiday homes

1. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (30 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
The price is £184
includes taxes & fees
30 Sept - 1 Oct
Family Stays: Middletown, CT
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

2. 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 £223
includes taxes & fees
21 Sept - 22 Sept
Newly Remodeled 1-BR Close to Everything yet Very Private
A wooden deck with chairs overlooking a calm lake surrounded by autumn foliage.

3. #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 £304
includes taxes & fees
20 Sept - 21 Sept
#24 Serenity A Lakefront Cottage Retreat
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

4. 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 £223
includes taxes & fees
14 Sept - 15 Sept
Once the old Schools house now a newly furnished Apartment
A bedroom with a bed, a painting of birds, a window with shutters, and a patterned rug.

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

The Cottage by the Woods -private getaway to relax
Meriden
The price is £473
includes taxes & fees
14 Sept - 15 Sept
The Cottage by the Woods -private getaway to relax
A two-story house with a front porch, a garage, and a well-maintained lawn.

6. 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, (18 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 £633
includes taxes & fees
21 Sept - 22 Sept
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
A modern kitchen with a central island, bar stools, and pendant lighting.

7. 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, (31 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 £766
includes taxes & fees
14 Sept - 15 Sept
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
A staircase with a handrail, a potted plant with yellow flowers, and a sign above the stairs.

8. Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Waterbury
8.0 out of 10, Very good, (1 review)
"I had an emergency and was only able to stay one night, but enjoyed my stay "
United States
Dirk N.
The price is £111
includes taxes & fees
21 Sept - 22 Sept
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A marina with multiple docks and boats, surrounded by residential buildings and greenery.

9. Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Fair Haven
7.6 out of 10, Good, (5 reviews)
"Thanks for hosting us! It was clean and nice. For future guests, a long body mirror might be nice but we had a wonderful time and appreciated you bringing us extra towels quickly!"
United States
Jamie S.
The price is £171
includes taxes & fees
14 Sept - 15 Sept
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
A modern living room with a flat-screen TV, a glass coffee table, and a staircase leading to another level.

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

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
9.2 out of 10, Wonderful, (30 reviews)
"Was a great stay"
United States
John S.
The price is £242
includes taxes & fees
9 Sept - 10 Sept
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
A front view of a house with a wooden staircase leading to a front door, a small porch area, and a garage door.

11. 1-bedroom vacation home 22 minutes from Quinnipiac University

1-bedroom vacation home 22 minutes from Quinnipiac University
Wolcott
9.6 out of 10, Exceptional, (4 reviews)
"Very clean and the host was great "
United States
David G.
The price is £299
includes taxes & fees
1 Oct - 2 Oct
1-bedroom vacation home 22 minutes from Quinnipiac University
A marina with multiple docks and boats, surrounded by residential buildings and greenery.

12. 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 £237
includes taxes & fees
14 Sept - 15 Sept
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
A modern kitchen with stainless steel appliances, a central island, and a dining area with a sofa.

13. #27- Luxury Collection

#27- Luxury Collection
Southington
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home, well designed and spacious rooms. Host was fantastic and communication was great! Thank you"
United States
C B.
The price is £345
includes taxes & fees
5 Oct - 6 Oct
#27- Luxury Collection
A dining area with a table, chairs, a refrigerator, and wall-mounted lights.

14. Cozy 1-bedroom house in lovely New Haven with AC close to Yale University

Cozy 1-bedroom house in lovely New Haven with AC close to Yale University
Fair Haven
5.6 out of 10, (4 reviews)
"Blankets where itchy and smelled dirty small room when whole house was listed"
United States
Isabella R.
The price is £97
includes taxes & fees
14 Sept - 15 Sept
Cozy 1-bedroom house in lovely New Haven with AC close to Yale University
A living room with a dark blue sofa, a round ottoman, a coffee table, and a TV on a stand. There is a large abstract painting on the wall and a window with curtains.

15. Cozy basement apartment with private bathroom, kitchen and entrance.

Cozy basement apartment with private bathroom, kitchen and entrance.
Marlborough
The price is £373
includes taxes & fees
14 Sept - 15 Sept
Cozy basement apartment with private bathroom, kitchen and entrance.
A spacious living room with a brown leather sofa, a dining area with a wooden table and chairs, and a kitchen with stainless steel appliances.

16. #11 - 4 Bedrooms, 3 Baths! Sleeps up to 8

#11 - 4 Bedrooms, 3 Baths! Sleeps up to 8
Plainville
10.0 out of 10, Exceptional, (3 reviews)
"Great weekend with friends!"
United States
Neil R.
The price is £472
includes taxes & fees
13 Sept - 14 Sept
#11 - 4 Bedrooms, 3 Baths! Sleeps up to 8
A living room with a blue sofa, a round coffee table, and a staircase.

17. The Game House Arcade – West Hartford

The Game House Arcade – West Hartford
West Hartford
10.0 out of 10, Exceptional, (1 review)
"Great location and well equipped. We will be back"
United States
Mike W.
The price is £359
includes taxes & fees
14 Sept - 15 Sept
The Game House Arcade – West Hartford

18. Prime West Hartford Center: Timeless Charm

Prime West Hartford Center: Timeless Charm
West Hartford
10.0 out of 10, Exceptional, (24 reviews)
"Great location and lots of room for grandkids to spread out and fun games for them to play with"
United States
Michael W.
The price is £400
includes taxes & fees
14 Sept - 15 Sept
Prime West Hartford Center: Timeless Charm
A room with a large window overlooking a coastal view, a beige sofa, and a small table with books and a vase.

19. Clear LI Sound waterview, Wedding pics, Yale&Beach

Clear LI Sound waterview, Wedding pics, Yale&Beach
East Shore
10.0 out of 10, Exceptional, (13 reviews)
"Great stay! Would definitely stay again! "
United States
Frankie O.
The price is £465
includes taxes & fees
14 Sept - 15 Sept
Clear LI Sound waterview, Wedding pics, Yale&Beach
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

20. Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is £434
includes taxes & fees
9 Sept - 10 Sept
Beachside Bliss w/ Game Room, Gym & Golf Green
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.
View all properties
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

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

10/10 Excellent
"EXCELENTE. HOTEL"
MARIVELISSE 2-night trip
Posted 2 hours ago
Holiday Inn Express Southington by IHG

Find out more about Middlefield

Middlefield Holiday Homes information

Number of reviews
9,927
Accommodation
291 Holiday Homes
Lowest Price
£54
Highest Price
£142