Photo by Simmie Reagor

Search Holiday Homes in Middletown

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Browse Select Middletown Holiday Homes

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (113)
"Was looking for a coastal retreat to enjoy a couple days with my daughter who lives near this location. This property had everything from a super clean, cozy studio with fridge and counters filled with surprising treats, incredible hot tub with lights in the trees, pool to cool off and little private beach to launch a paddlleboard and kayak, or hang out at night with a burn pit. If you are just a beach person and want toes in the sand and to swim in the ocean, this area is not for you....
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Patchogue River Retreat, 8 minute walk to West Beach
10.0 out of 10, Exceptional, (6)
"House was very nice. Location is great. Easy walk to beach and convenient to Westbrook center."
Patchogue River Retreat, 8 minute walk to West Beach
Mountaintop Horse Farm with Heated Pool
10.0 out of 10, Exceptional, (17)
"We enjoyed meeting and spending time with all the lovely animals on this quaint farm. Apartment was so lovely and spacious. Highly recommend stopping by for a stay."
Mountaintop Horse Farm with Heated Pool
Lovely Westbrook Home w/ Patio - Walk to Beach!
10.0 out of 10, Exceptional, (1)
"Beautifully decorated comfortable and clean would definitely rent again"
Lovely Westbrook Home w/ Patio - Walk to Beach!
Quiet Connecticut Retreat w/ Pool, Deck & Fire Pit
Quiet Connecticut Retreat w/ Pool, Deck & Fire Pit
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
10.0 out of 10, Exceptional, (2)
"Quality property with a top notch owner."
The price is £679
includes taxes & fees
23 Jun - 24 Jun
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Trout Brook Trail 2 · Sprawling Classic New England Home
10.0 out of 10, Exceptional, (11)
"In town for our daughters graduation. The home was perfect in every way! Clean, all rooms are a good size, nicely situated kitchen, beautiful deck for socializing, our guests did not feel like we were on top of each other. Plenty of blankets, towels, kitchen supplies. Everything in good working condition. The home has antique charm with updated benefits. The host Mark was easy to communicate with. We walked to town and loved every part of our weekend! Its a must! Thank you Mark for sharing Trout...
Trout Brook Trail 2 · Sprawling Classic New England Home
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
9.0 out of 10, Wonderful, (69)
"We very much enjoyed our stay and the host had everything prepared for us. The check in/out process was very easy as well!"
The price is £660
includes taxes & fees
14 Jul - 15 Jul
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
gorgeous victorian direct ocean front single family six bedroom, ten rooms
10.0 out of 10, Exceptional, (51)
"Wonderful host. Easy communication. Great house."
gorgeous victorian direct ocean front single family six bedroom, ten rooms
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
10.0 out of 10, Exceptional, (16)
"My month-long stay was absolutely wonderful. Hunter was an amazing, proactive host. The weather wasn't cooperative in the beginning of my stay, but Hunter went above and beyond to make sure whatever issues arose were taken care of and I couldn't be happier to have made this choice. I will definitely be back!"
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
Cozy Westbrook Vacation Rental - Walk to Beach!
10.0 out of 10, Exceptional, (3)
"Everything one would need for a beach vacation. Responsive contact person."
Cozy Westbrook Vacation Rental - Walk to Beach!
Amazing Lakefront Property
10.0 out of 10, Exceptional, (15)
"This was my second go round staying at this property. My family and I enjoyed it the first time. More so the second time with the upgrades. Being familiar with the area was a great help. This time we went in the lake and enjoyed ourselves. We are looking forward to returning back again. Thank you Raymond for letting us stay at your property. Richard and Joanne"
Amazing Lakefront Property
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
9.8 out of 10, Exceptional, (107)
"A number of friends and I stayed here to be nearby our friends wake and memorial service. It was a really nice homely, quiet space that had plenty of room for everyone and the view over the river is gorgeous. Would love to come back sometime for more uplifting circumstances"
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
Massive 5 Bedrooms: 3King 2Queen
The price is £642
includes taxes & fees
9 Jul - 10 Jul
Massive 5 Bedrooms: 3King 2Queen
Modern & Cozy Cape | 4 Bedroom House | Central Location
10.0 out of 10, Exceptional, (3)
"It was good experience from start to finish. I would recommend it to others."
The price is £246
includes taxes & fees
11 Jul - 12 Jul
Modern & Cozy Cape | 4 Bedroom House | Central Location
Saltwater Gospel-Indian Town, Old Saybrook CT
Saltwater Gospel-Indian Town, Old Saybrook CT
Essex Village home within walking distance to downtown.
10.0 out of 10, Exceptional, (4)
"Our party of four enjoyed our stay in this charming, well appointed home. There was plenty of room for morning coffee on the front porch or visiting in the living room. The house was very clean and the beds comfortable. We had one minor issue and our host answered promptly and remedied the situation. Fred was also very helpful with all of our queries. Highly recommend a visit to Essex and a stay in this charming cottage."
Essex Village home within walking distance to downtown.
Near Yale 8 beds Gaming Room
Near Yale 8 beds Gaming Room
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
9.8 out of 10, Exceptional, (38)
"Great place. Cozy cottage!"
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
lakefront estate
3.8 out of 10, (8)
"Overall do not stay in this house! They are scamming people! They say they are military family yet took advantage of one!! Still owe me my refund and refuse to answer VRBO to give the okay to refund my money! This place was not clean it was very unsanitary and there were drug paraphernalia in the backyard! Towels wet and dirty on the bathroom floor and one of the bedrooms the sheets were dirty in the floor claimed that the house keeper cleaned it! The pool was disgusting!! I have videos pictures...
lakefront estate
Don't see what you're looking for?
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.

Other property types in Middletown

Cozy newly remodeled home close to major amenities in Connecticut a
8.4 out of 10, Very good, (10)
"We stayed here while visiting our family. The property was clean, quiet and exactly as described. The kitchen seemed well stocked. The huge washing machine/dryer was great after our cross country drive. There are just a few things to be aware of: the bathroom is on the second floor. The bed we slept on was not too too comfortable (a little firm for our tastes). The single bed was very firm. Other than that it was a nice place to stay."
Cozy newly remodeled home close to major amenities in Connecticut a
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (113)
"Was looking for a coastal retreat to enjoy a couple days with my daughter who lives near this location. This property had everything from a super clean, cozy studio with fridge and counters filled with surprising treats, incredible hot tub with lights in the trees, pool to cool off and little private beach to launch a paddlleboard and kayak, or hang out at night with a burn pit. If you are just a beach person and want toes in the sand and to swim in the ocean, this area is not for you....
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Patchogue River Retreat, 8 minute walk to West Beach
10.0 out of 10, Exceptional, (6)
"House was very nice. Location is great. Easy walk to beach and convenient to Westbrook center."
Patchogue River Retreat, 8 minute walk to West 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.

Middletown Holiday Homes information

Number of reviews
406
Accommodation
283 Holiday Homes
Lowest Price
£246
Highest Price
£679

Middletown Hotel Reviews
Expedia verified reviews