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Holiday Homes in Middletown

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Featured Holiday Homes in Middletown and around

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Smart TV
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
9.4 out of 10, Exceptional, (10)
"Beautiful condo as advertised, great communication."
The price is €265
includes taxes & fees
30 Sept - 1 Oct
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
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, (6)
"The house was clean, comfortable and convenient to many of the things we wanted to do. It was located in a nice quiet neighborhood. The beds were very comfortable. There were many restaurants 10-20 minutes away. We enjoyed our stay."
The price is €290
includes taxes & fees
8 Oct - 9 Oct
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Dining
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
9.8 out of 10, Exceptional, (24)
"We booked late in summer and spent 2 nights on beach road when we should have stayed longer. Fantastic location, great neighborhood, clean and comfortable beach house, my wife and I very much enjoyed the house and the shore. Can’t wait to book again!"
The price is €678
includes taxes & fees
13 Oct - 14 Oct
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Waterfront Beach House
Terrace/patio
Waterfront Beach House
9.6 out of 10, Exceptional, (36)
"Wishing i had brought my daughter and grandchildren. Such a family friendly environment. Clean, organized, comfortable "
Waterfront Beach House
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Beach nearby, sun-loungers, beach towels
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
9.2 out of 10, Wonderful, (80)
"We enjoyed our long weekend stay at the Count House. Its location was perfect ... easy beach access, close to the highway, etc. Everything we needed was supplied for us to enjoy the beach, cook our meals, or play games. There was only one full-size kayak with paddle and the paddle board paddle was broken (but we used it by kneeling on the board!). We would definitely return."
The price is €396
includes taxes & fees
3 Oct - 4 Oct
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Living area
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
9.8 out of 10, Exceptional, (6)
"We were staying in CT for my granddaughters Nationals SB tournament The location was great, it was Close to everything we needed We would def. Stay again due to the easy check in, all the extra amenities Lynn supplies along with her quick responses to our communication with her. If we had to make a suggestion, it would be a to add more air conditioners as the summertime can get quite hot We enjoyed our stay"
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Historic Essex Home w/ Large Yard Near Downtown!
TV
Historic Essex Home w/ Large Yard Near Downtown!
9.8 out of 10, Exceptional, (39)
"All bedrooms up were difficult with luggage. Fully equipped for an extended stay would be convenient. Very close to marina and shopping."
Historic Essex Home w/ Large Yard Near Downtown!
Beautiful 3BR, Rare Find, Clean & Guest Favorite
Fridge, microwave, oven, stovetop
Beautiful 3BR, Rare Find, Clean & Guest Favorite
2.0 star property
The price is €296
includes taxes & fees
30 Sept - 1 Oct
Beautiful 3BR, Rare Find, Clean & Guest Favorite
15mins to Hartford, Home in Manchester w/ King Bed
Fridge, microwave, oven, cookware/dishes/utensils
15mins to Hartford, Home in Manchester w/ King Bed
2.0 star property
The price is €304
includes taxes & fees
30 Sept - 1 Oct
15mins to Hartford, Home in Manchester w/ King Bed
Riverview Grandeur Tranquility & Luxury Essex CT
Fridge, microwave, oven, stovetop
Riverview Grandeur Tranquility & Luxury Essex CT
2.0 star property
9.6 out of 10, Exceptional, (4)
"This property is well maintained, conveniently located, has superb amenities and has beautiful views of the CT river. I recommend it highly and without qualification,"
Riverview Grandeur Tranquility & Luxury Essex CT
15mins to Hartford, Home in Manchester w/ King Bed
Fridge, microwave, oven, stovetop
15mins to Hartford, Home in Manchester w/ King Bed
2.0 star property
The price is €304
includes taxes & fees
30 Sept - 1 Oct
15mins to Hartford, Home in Manchester w/ King Bed
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Property grounds
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (123)
"Our stay was incredible! The property was gorgeous- even with the home owners on property we barely saw them. We had full, private access to the backyard space- beach, pool, hot tub, fire pit, etc- all to ourselves. The property was clean and inviting and we will definitely go back. Everyone was so friendly and the area is picturesque. "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Seaside Serenity: Relaxation by Jacob's Beach
TV, offices
Seaside Serenity: Relaxation by Jacob's Beach
9.2 out of 10, Wonderful, (28)
"My family drove down to CT from Rochester NY for family day at my daughter’s college. When we arrived at your home, we were very pleased with the location, surrounding neighborhood, the town the house was located, and the house itself. We were very comfortable and felt as if all our amenities were met. We really enjoyed walking to Jacob’s Beach—such a pretty place. We will definitely stay at this home again. "
Seaside Serenity: Relaxation by Jacob's Beach
Waterfront House with picture-perfect views from all 3 levels.
Interior
Waterfront House with picture-perfect views from all 3 levels.
9.6 out of 10, Exceptional, (72)
"It was lovely falling asleep to sound of waves every night. The house was comfortable and clean. The owners, Carolyn and Jon, were responsive and helpful. We had a great week."
Waterfront House with picture-perfect views from all 3 levels.
Cozy newly remodeled home close to major amenities in Connecticut a
Private kitchen
Cozy newly remodeled home close to major amenities in Connecticut a
8.2 out of 10, Very good, (15)
"We came to ct from South Carolina for my nieces wedding. E didn’t know what to expect. When we got there we were pleasantly surprised. The house was clean had a little fenced in patio. Check in was easy. Had easy access to the highway. The only thing I wish was that it had a first floor bathroom. But the house was perfect. Thank you. "
Cozy newly remodeled home close to major amenities in Connecticut a
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Fridge, microwave, oven, stovetop
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
10.0 out of 10, Exceptional, (5)
"To say that the property was in pristine condition and impeccably designed and decorated would be understatements. Everything was perfect and if we could have stayed in this luxurious home longer, we would have. The property was a perfect launching point for our visit to Powder Ridge for mountain biking and to visit other nearby sites in the beautiful area. The host responded to inquiries without delay and was a pleasure to interact with. We highly recommend without hesitation!"
The price is €784
includes taxes & fees
30 Sept - 1 Oct
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Lakefront Home, Close to Mt Southington!
Fridge, microwave, stovetop, dishwasher
Lakefront Home, Close to Mt Southington!
10.0 out of 10, Exceptional, (12)
"Staff very much enjoyed the atmosphere after long days of work. Wonderful Ownership. Thank you so much Susan!"
Lakefront Home, Close to Mt Southington!
Grammy's Lake House w/ Private Waterfront Access
Dining
Grammy's Lake House w/ Private Waterfront Access
10.0 out of 10, Exceptional, (7)
"Spacious, with well supplied kitchen and comfortable beds. We enjoyed gazing at the lake from second floor rooms and front porch. We drove to downtown East Hampton which is a pleasant throwback to small town America of the '50s.. "
Grammy's Lake House w/ Private Waterfront Access
NEW! Seaside Beach Haven with a private beach!
Property grounds
NEW! Seaside Beach Haven with a private beach!
10.0 out of 10, Exceptional, (9)
"It was absolutely gorgeous. We truly enjoyed our stay. 5 ⭐️"
NEW! Seaside Beach Haven with a private beach!
Heavenly Home in New Haven
Interior
Heavenly Home in New Haven
8.8 out of 10, Excellent, (15)
"The property was prepared well and we enjoyed our stay. Thanks"
The price is €564
includes taxes & fees
30 Sept - 1 Oct
Heavenly Home in New Haven
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See all available properties in Middletown
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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Other property types in Middletown

Cozy newly remodeled home close to major amenities in Connecticut a
Private kitchen
Cozy newly remodeled home close to major amenities in Connecticut a
8.2 out of 10, Very good, (15)
"We came to ct from South Carolina for my nieces wedding. E didn’t know what to expect. When we got there we were pleasantly surprised. The house was clean had a little fenced in patio. Check in was easy. Had easy access to the highway. The only thing I wish was that it had a first floor bathroom. But the house was perfect. Thank you. "
Cozy newly remodeled home close to major amenities in Connecticut a
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Beach nearby, sun-loungers, beach towels
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
9.2 out of 10, Wonderful, (80)
"We enjoyed our long weekend stay at the Count House. Its location was perfect ... easy beach access, close to the highway, etc. Everything we needed was supplied for us to enjoy the beach, cook our meals, or play games. There was only one full-size kayak with paddle and the paddle board paddle was broken (but we used it by kneeling on the board!). We would definitely return."
The price is €396
includes taxes & fees
3 Oct - 4 Oct
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Beach nearby, sun-loungers, beach towels
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, (99)
"My family and I had a great stay at this adorable beach house! It had plenty of room for our family of 6. The private beach was just a short walk around the corner! "
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
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.