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Compare 300 Vacation Homes in Middletown with updated reviews, rates, and availability.

Charming 2-bedroom townhome
Room
Charming 2-bedroom townhome
2.0 star property
9.6 out of 10, Exceptional, (5)
"The home was beautiful and I would stay there again."
The price is AED 533
AED 806 total
includes taxes & fees
20 Nov - 21 Nov
Charming 2-bedroom townhome
Waterfront Beach House
Beach
Waterfront Beach House
9.6 out of 10, Exceptional, (39)
"This was perfect for us. We had a family funeral and this was a nice retreat. We would stay again for sure. "
Waterfront Beach House
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Pool
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (126)
"We stayed here for an anniversary weekend away and found the property and neighborhood to be amazing. We enjoyed the hot tub, pool and firepit and went kayaking in the afternoon. Enjoyed amazing sunsets from the deck; Adam gave us spot-on restaurant recommendations. I don't know if the supply of snacks is standard or an anniversary "special", but all in all this place was a wonderful find. Thank you!!"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Beach
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
9.0 out of 10, Wonderful, (85)
"We liked the house which is ideal for a large group. But we were disappointed that the water views shown in the photo gallery did not exist as views from the house directly. "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Historic Essex Home w/ Large Yard Near Downtown!
Essex Vacation Rental | 2BR | 1.5BA | Steps Required | 1,400 Sq Ft
Historic Essex Home w/ Large Yard Near Downtown!
9.8 out of 10, Exceptional, (40)
"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!
15mins to Hartford, Home in Manchester w/ King Bed
Exterior
15mins to Hartford, Home in Manchester w/ King Bed
2.0 star property
10.0 out of 10, Exceptional, (1)
"Very spacious location. Ideal fit for our plans. "
The price is AED 687
AED 1,348 total
includes taxes & fees
21 Nov - 22 Nov
15mins to Hartford, Home in Manchester w/ King Bed
Amazing Lakefront Property
Dining
Amazing Lakefront Property
9.8 out of 10, Exceptional, (23)
"Great views and a good central location for day trips 👌. "
Amazing Lakefront Property
Lakefront Home, Close to Mt Southington!
Wolcott Vacation Rental | 3BR | 2BA | 1,176 Sq Ft | Stairs Required
Lakefront Home, Close to Mt Southington!
10.0 out of 10, Exceptional, (13)
"Staff very much enjoyed the atmosphere after long days of work. Wonderful Ownership. Thank you so much Susan!"
Lakefront Home, Close to Mt Southington!
Summer at the Haddam House
Property grounds
Summer at the Haddam House
10.0 out of 10, Exceptional, (49)
"Hands down , Very nice property , highly recommend staying at this location . You won’t be let down . "
Summer at the Haddam House
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Living Room
Charming 3BR Hilltop House, Newly Remodeled with Arcade
10.0 out of 10, Exceptional, (18)
"So glad we found this property to accommodate our family of six for the weekend. It was cozy, updated and immaculately clean. The owners seem to have thought of everything and clearly care about providing an exceptional experience. Highly recommend!"
Charming 3BR Hilltop House, Newly Remodeled with Arcade
NEW! Seaside Beach Haven with a private beach!
Gorgeous spot!
NEW! Seaside Beach Haven with a private beach!
10.0 out of 10, Exceptional, (11)
"Good"
NEW! Seaside Beach Haven with a private beach!
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Exterior
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
10.0 out of 10, Exceptional, (2)
"Started with Kristine greeting us as we drove in. Was accommodating to our requests and was very quick to reply to our few messages. Clothes dryer is very small. Short walk to a great park and beach."
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Living area
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
9.6 out of 10, Exceptional, (11)
"Very nice and clean family was visiting my daughter at the University of New Haven was also very close "
The price is AED 533
AED 1,020 total
includes taxes & fees
3 Dec - 4 Dec
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Guilford home -self check in, off-street parking
Exterior
Guilford home -self check in, off-street parking
9.4 out of 10, Exceptional, (8)
"The property was nice, clean and comfortable. "
Guilford home -self check in, off-street parking
Near Yale 8 beds Gaming Room
Exterior
Near Yale 8 beds Gaming Room
The price is AED 2,020
AED 4,035 total
includes taxes & fees
20 Nov - 21 Nov
Near Yale 8 beds Gaming Room
NEW-Another Fun Downtown Location 1st floor
Exterior detail
NEW-Another Fun Downtown Location 1st floor
2.0 star property
10.0 out of 10, Exceptional, (6)
"This was our second stay at this VRBO and hope to stay again on return trips to the area."
NEW-Another Fun Downtown Location 1st floor
Beautiful Home - 3 King & 2 Queen - Rare Find
Living area
Beautiful Home - 3 King & 2 Queen - Rare Find
2.0 star property
The price is AED 959
AED 2,426 total
includes taxes & fees
18 Nov - 19 Nov
Beautiful Home - 3 King & 2 Queen - Rare Find
Charming year-round beach home in Indian Town, Old Saybrook
front of home
Charming year-round beach home in Indian Town, Old Saybrook
The price is AED 1,469
AED 3,115 total
includes taxes & fees
16 Nov - 17 Nov
Charming year-round beach home in Indian Town, Old Saybrook
gorgeous victorian direct ocean front single family six bedroom, ten rooms
Sunset 🌅 Living room view .
gorgeous victorian direct ocean front single family six bedroom, ten rooms
10.0 out of 10, Exceptional, (58)
"Beautiful home with even more beautiful ocean view. "
gorgeous victorian direct ocean front single family six bedroom, ten rooms
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!
Exterior image
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!
10.0 out of 10, Exceptional, (23)
"This was a great spot to stay with friends, with great separate living areas and a great central living room to gather. The location is minutes from downtown Guilford and was very convenient to do and see everything. I would not recommend bringing small children because there is so much beautiful artwork all around the house, but it’s a beautiful retreat for older kids/teens and adults! "
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!
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
Living room
Cozy newly remodeled home close to major amenities in Connecticut a
8.4 out of 10, Very Good, (16)
"I love staying here. Each visit I bring something new from Louisiana and leave it for the next guest. The cooking supplies are admirable for a home, and especially so for a home away-from-home. We couldn't find a better place to stay. The beds are super comfy, though the furniture requires extra padding. Fortunately there are lots of blankets to use as cishioning."
Cozy newly remodeled home close to major amenities in Connecticut a
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Welcome to our cute getaway
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
10.0 out of 10, Exceptional, (68)
"We really enjoyed our time away at this wonderful cottage!"
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Miscellaneous
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
10.0 out of 10, Exceptional, (13)
"This was a great spot to stay with my wife, another couple, and my dog! The house is small - especially downstairs. But it is extremely well thought out and space is used as effectively as can be. Upstairs had 2 good sized bedrooms with king beds and a nicely renovated bathroom with a great shower. The house is located in a small, cute, and a bit of an unusual neighborhood. Very quiet. Very safe feel. But not too good for much dog walking and parking is super tight. Owner was very good with...
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
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.