A forested landscape with a winding dirt road and power lines.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Middletown holiday homes

Veterans Park, near the house

1. 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 £204
includes taxes & fees
28 Oct - 29 Oct
Family Stays: Middletown, CT
A modern living room with a sofa, a dining table, and a massage chair.

2. #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 £374
includes taxes & fees
13 Oct - 14 Oct
#29 - Modern 5 Bedroom/2 Bath
A two-story house with a front porch, a garage, and a well-maintained lawn.

3. 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 £622
includes taxes & fees
5 Oct - 6 Oct
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

4. 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 £227
includes taxes & fees
6 Oct - 7 Oct
Newly Remodeled 1-BR Close to Everything yet Very Private
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

5. 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)
"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
5 Oct - 6 Oct
Once the old Schools house now a newly furnished Apartment
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 £483
includes taxes & fees
3 Oct - 4 Oct
The Cottage by the Woods -private getaway to relax
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, (33 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 £782
includes taxes & fees
5 Oct - 6 Oct
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 £113
includes taxes & fees
14 Oct - 15 Oct
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A living room with a staircase, red and grey sofas, a coffee table, and a red door.

9. Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
9.8 out of 10, Exceptional, (10 reviews)
"Great place"
United States
John S.
The price is £229
includes taxes & fees
8 Oct - 9 Oct
Modern & Cozy Cape | 4 Bedroom House | Central Location
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

10. Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (3 reviews)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
The price is £544
includes taxes & fees
30 Oct - 31 Oct
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
A modern living room with a sofa, a coffee table, and a rug.

11. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
9.8 out of 10, Exceptional, (10 reviews)
"Good location"
United States
Arthur
The price is £93
includes taxes & fees
11 Oct - 12 Oct
Entire guest suite in South Windsor, Connecticut
Dining

12. Prime West Hartford Center: Timeless Charm

Prime West Hartford Center: Timeless Charm
West Hartford
10.0 out of 10, Exceptional, (25 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 £419
includes taxes & fees
13 Oct - 14 Oct
Prime West Hartford Center: Timeless Charm
A modern living room with a flat-screen TV, a glass coffee table, and a staircase leading to another level.

13. 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 £233
includes taxes & fees
25 Oct - 26 Oct
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
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 £345
includes taxes & fees
20 Oct - 21 Oct
#27- Luxury Collection
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
8 Oct - 9 Oct
Cozy basement apartment with private bathroom, kitchen and entrance.
A two-story house with a porch, a front door with a wreath, and a small garden area.

16. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (9 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is £249
includes taxes & fees
8 Oct - 9 Oct
Bear Retreat - 2-bedroom house in Waterbury
A modern living room with a fireplace, leather sofas, a blue armchair, and large windows.

17. #30 - Spacious & Cozy!

#30 - Spacious & Cozy!
Southington
6.8 out of 10, (5 reviews)
"the house was great for our needs - it was nicely furnished fully stocked with the essentials in the kitchen. the host checked in when it was especially cold to ensure the heat and water were working correctly. the living room was very comfortable with leather reclining chairs and a gas fireplace that heated the room very well. We enjoyed how easy our stay was and recommend this location "
United States
Kaity B.
The price is £371
includes taxes & fees
7 Oct - 8 Oct
#30 - Spacious & Cozy!
A covered porch with white rocking chairs and a table, a blue ceiling, and a view of the garden.

18. Charming New England Home in West Hartford Center

Charming New England Home in West Hartford Center
West Hartford
10.0 out of 10, Exceptional, (32 reviews)
"Great location. Beautiful, comfortable home."
United States
karen
The price is £381
includes taxes & fees
4 Oct - 5 Oct
Charming New England Home in West Hartford Center
A modern dining area with a marble table, white chairs, and a chandelier.

19. Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford

Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
Manchester
9.2 out of 10, Wonderful, (5 reviews)
"House was great for our family stay!"
United States
Kim A.
The price is £236
includes taxes & fees
4 Oct - 5 Oct
Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
A covered patio with a dining table, chairs, and a grill.

20. Prime West Hartford Center Location: Historic Gem

Prime West Hartford Center Location: Historic Gem
West Hartford
10.0 out of 10, Exceptional, (36 reviews)
"We loved being so close to downtown West Hartford. The house had everything we needed for a fun graduation weekend."
United States
Trish
The price is £455
includes taxes & fees
4 Oct - 5 Oct
Prime West Hartford Center Location: Historic Gem
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 Middletown Hotel Reviews

Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

10/10 Excellent
"No es un lugar Waoo, pero si tienes mascotas y llevas tu detergentes para limpiar está bien, yo acostumbro a llevar mis sábanas propias para no quejarme, aunque no tengo ninguna queja que dar."
Bettyzu 3-night trip
Posted 1 hour ago
Motel 6 New Haven - Branford, CT

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
250
Accommodation
341 Holiday Homes
Lowest Price
£93
Highest Price
£782