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

Holiday Homes in Middlefield

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Middlefield holiday homes

A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

1. 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 €266
includes taxes & fees
5 Oct - 6 Oct
Newly Remodeled 1-BR Close to Everything yet Very Private
A wooden deck with chairs overlooking a calm lake surrounded by autumn foliage.

2. #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 €303
includes taxes & fees
28 Sept - 29 Sept
#24 Serenity A Lakefront Cottage Retreat

3. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (31 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
The price is €229
includes taxes & fees
29 Sept - 30 Sept
Family Stays: Middletown, CT
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
9.2 out of 10, Wonderful, (15 reviews)
"This apartment was wonderful - clean, well stocked, and cute. Aside from the proximity to the train tracks (although earplugs were thoughtfully provided), the location was great - close to the highway and more importantly Dairy Queen."
United States
Becky P.
The price is €266
includes taxes & fees
27 Sept - 28 Sept
Once the old Schools house now a newly furnished Apartment
A modern living room with a sofa, a dining table, and a massage chair.

5. #29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.0 out of 10, Wonderful, (7 reviews)
"Great place! "
United States
Gail R.
The price is €437
includes taxes & fees
7 Oct - 8 Oct
#29 - Modern 5 Bedroom/2 Bath
A bedroom with a bed, a nightstand, a lamp, and a wooden wardrobe.

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

The Cottage by the Woods -private getaway to relax
Meriden
The price is €571
includes taxes & fees
4 Oct - 5 Oct
The Cottage by the Woods -private getaway to relax
A modern kitchen with white cabinets, stainless steel appliances, and a herringbone-patterned backsplash.

7. #26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home
Plainville
10.0 out of 10, Exceptional, (5 reviews)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
#26 Beautifully Renovated 2 BR Home
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 €133
includes taxes & fees
27 Sept - 28 Sept
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A two-story house with a front porch, a garage, and a well-maintained lawn.

9. 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, (19 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 €724
includes taxes & fees
28 Sept - 29 Sept
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
A two-story house with a porch, a front door with a wreath, and a small garden area.

10. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (8 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is €299
includes taxes & fees
8 Oct - 9 Oct
Bear Retreat - 2-bedroom house in Waterbury
A modern kitchen with a central island, bar stools, and pendant lighting.

11. 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, (32 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 €915
includes taxes & fees
6 Oct - 7 Oct
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
A dining area with a table, chairs, a refrigerator, and wall-mounted lights.

12. 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 €102
includes taxes & fees
29 Sept - 30 Sept
Cozy 1-bedroom house in lovely New Haven with AC close to Yale University
A front view of a house with a wooden staircase leading to a front door, a small porch area, and a garage door.

13. 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 €360
includes taxes & fees
1 Oct - 2 Oct
1-bedroom vacation home 22 minutes from Quinnipiac University
A modern kitchen with stainless steel appliances, a central island, and a dining area with a sofa.

14. #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 €415
includes taxes & fees
5 Oct - 6 Oct
#27- Luxury Collection
A marina with multiple docks and boats, surrounded by residential buildings and greenery.

15. 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 €205
includes taxes & fees
28 Sept - 29 Sept
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
A room with a wooden floor, a white door, and a closet with hanging clothes and a folded towel.

16. Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale

Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale
Newhallville
The price is €352
includes taxes & fees
30 Sept - 1 Oct
Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale
A kitchen with white cabinets, stainless steel appliances, a kettle on the stove, and a refrigerator with magnets.

17. Charming 2-bedroom cottage with AC in Westbrook

Charming 2-bedroom cottage with AC in Westbrook
Westbrook
Charming 2-bedroom cottage with AC in Westbrook
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.

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

Cozy basement apartment with private bathroom, kitchen and entrance.
Marlborough
The price is €446
includes taxes & fees
28 Sept - 29 Sept
Cozy basement apartment with private bathroom, kitchen and entrance.
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 €519
includes taxes & fees
28 Sept - 29 Sept
Clear LI Sound waterview, Wedding pics, Yale&Beach
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
"Great location, staff were so helpful and accommodating! Got free water and coffee! Parking was very accessible! Great room!"
Hayley 1-night trip
Posted less than an hour ago
New Haven Hotel

Find out more about Middlefield

Middlefield Holiday Homes information

Number of reviews
128
Accommodation
286 Holiday Homes
Lowest Price
€102
Highest Price
€915