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Holiday Homes in Middletown

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Middletown

#24 *Serenity* A Lakefront Cottage Retreat
Dining

#24 *Serenity* A Lakefront Cottage Retreat

9.8 out of 10, Exceptional, (18)
"Quiet and peaceful cottage. Clean and well equipped with everything we needed. Great location to sight see and visit local attractions. Loved sitting relaxing by the lake."
The price is NZ$587
includes taxes & fees
3 Sept - 4 Sept
#24 *Serenity* A Lakefront Cottage Retreat
Cozy Guest Suite in Historic Home
Interior

Cozy Guest Suite in Historic Home

The price is NZ$328
includes taxes & fees
17 Aug - 18 Aug
Cozy Guest Suite in Historic Home
Family Stays: Middletown, CT
Fridge, microwave, oven, stovetop

Family Stays: Middletown, CT

10.0 out of 10, Exceptional, (9)
"Our experience with this facility, from online service to exiting the residence, was the most pleasurable experience, for staying in accommodations when traveling!!The owner was a complete gentleman and it was absolutely wonderful experience to meet and talk with him."
The price is NZ$493
includes taxes & fees
3 Sept - 4 Sept
Family Stays: Middletown, CT
#29 - Modern 5 Bedroom/2 Bath
Fridge, microwave, oven, stovetop

#29 - Modern 5 Bedroom/2 Bath

10.0 out of 10, Exceptional, (4)
"Beautiful home and well suited for a peaceful stay. Great neighborhood and a wonderful how. Would recommend the property to anyone."
The price is NZ$772
includes taxes & fees
18 Aug - 19 Aug
#29 - Modern 5 Bedroom/2 Bath
Modern Luxury, The Perfect Getaway Awaits
Fridge, oven, stovetop, dishwasher

Modern Luxury, The Perfect Getaway Awaits

10.0 out of 10, Exceptional, (2)
"Super clear, spacious, house looks just like the photos. Very easy communication with the host. Thank you!"
The price is NZ$911
includes taxes & fees
17 Aug - 18 Aug
Modern Luxury, The Perfect Getaway Awaits
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Beach nearby

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

10.0 out of 10, Exceptional, (1)
"This was a great find so close to home when my family needed a place to stay for a week. The house was clean, inviting and the communication with the property manager was amazing! Very fast to respond!"
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Rogers Lake House (87) · CT College+Beach+USCGA
Property grounds

Rogers Lake House (87) · CT College+Beach+USCGA

10.0 out of 10, Exceptional, (2)
"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"
The price is NZ$1,263
includes taxes & fees
28 Aug - 29 Aug
Rogers Lake House (87) · CT College+Beach+USCGA
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Beach nearby, sun-loungers, beach towels

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

9.8 out of 10, Exceptional, (6)
"We stayed for a week and the house was perfect. Comfortable, so clean, very well stocked, really nice decor and a fantastic location. Host was very helpful and responsive. Highly recommend and we will definitely be back. "
The price is NZ$885
includes taxes & fees
3 Sept - 4 Sept
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Terrace/patio

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

9.6 out of 10, Exceptional, (132)
"Very much enjoyed our trip! "
The price is NZ$1,253
includes taxes & fees
19 Aug - 20 Aug
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Peace Barn in the heart of the CT River Valley
Outdoor dining

Peace Barn in the heart of the CT River Valley

2.0 star property
8.6 out of 10, Excellent, (4)
"The grounds were beautiful Everything else for me and my family’ was awful and should not be rented as a vrbo. Lots of bugs. The upstairs bathroom had no water pressure or hot water. The upstairs bedroom window and screen were duct taped shut. The kitchen was a mishmash of things that didn’t work. The house did smell of mold. The only thing this property has to offer is the lake and the land the lodging was terrible and not at all comfortable. And the lights were terrible, if you could even...
The price is NZ$1,194
includes taxes & fees
17 Aug - 18 Aug
Peace Barn in the heart of the CT River Valley
Spacious Lakefront Home|Bikes|Hot Tub| Kayak|Group
TV, fireplace

Spacious Lakefront Home|Bikes|Hot Tub| Kayak|Group

Spacious Lakefront Home|Bikes|Hot Tub| Kayak|Group
Cozy basement apartment with private bathroom, kitchen and entrance.
Smart TV

Cozy basement apartment with private bathroom, kitchen and entrance.

The price is NZ$813
includes taxes & fees
28 Aug - 29 Aug
Cozy basement apartment with private bathroom, kitchen and entrance.
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 NZ$433
includes taxes & fees
29 Aug - 30 Aug
Shoreline Oasis
Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT
Fridge, microwave, oven, stovetop

Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT

10.0 out of 10, Exceptional, (1)
"Spacious, clean and comfortable home. Nice neighborhood near a nice park and trails . Beds were comfortable, kitchen had the pots and pans we needed for dinner and breakfast. Perfect space for us and our 3 adult boys. "
The price is NZ$819
includes taxes & fees
18 Aug - 19 Aug
Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT
Modern & Cozy Cape | 4 Bedroom House | Central Location
Fridge, microwave, oven, stovetop

Modern & Cozy Cape | 4 Bedroom House | Central Location

10.0 out of 10, Exceptional, (5)
"We had a great stay in this house. It provided everything we needed for a comfortable and enjoyable visit. All the rooms were clean, tidy, and well-maintained, creating a welcoming environment. The host was exceptionally helpful and quick to respond to any questions or needs we had, which made our experience even better. We highly recommend this house for anyone looking for a hassle-free and pleasant stay."
The price is NZ$540
includes taxes & fees
3 Sept - 4 Sept
Modern & Cozy Cape | 4 Bedroom House | Central Location
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (11)
"House was great & close to where we needed to be. "
The price is NZ$515
includes taxes & fees
7 Sept - 8 Sept
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Historic New England home ,Reunions Beach pass
Fridge, microwave, oven, stovetop

Historic New England home ,Reunions Beach pass

9.2 out of 10, Wonderful, (88)
"House was perfect for family get together. Enjoyed walking into town for afternoon shopping and dining."
The price is NZ$1,074
includes taxes & fees
7 Sept - 8 Sept
Historic New England home ,Reunions Beach pass
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 NZ$1,366
includes taxes & fees
18 Aug - 19 Aug
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Microwave, electric kettle, cookware/dishes/utensils, paper towels

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

10.0 out of 10, Exceptional, (3)
"Great place in a very nice part of the city. Walkable and lots to do around, and a reasonable parking garage right across the street. Apartment was clean, comfy and easily accessible."
The price is NZ$399
includes taxes & fees
17 Aug - 18 Aug
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Private Apartment in Berlin
Fridge, microwave, oven, stovetop

Private Apartment in Berlin

2.0 star property
9.2 out of 10, Wonderful, (5)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
The price is NZ$674
includes taxes & fees
8 Sept - 9 Sept
Private Apartment in Berlin
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

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

10/10 Excellent
"Close to Yale campus"
Yaping 3-night trip
Posted 20 hours ago
Omni New Haven Hotel at Yale