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Compare 313 Vacation Homes in Middletown with updated reviews, rates, and availability.

Cozy Westbrook Vacation Rental - Walk to Beach!

10.0 out of 10, Exceptional, (11)
"Stayed at this house for a weekend after Christmas. It was great! Perfect location and easy to get everywhere! Would love to stay again."
Cozy Westbrook Vacation Rental - Walk to Beach!

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

9.4 out of 10, Exceptional, (13)
"I had such a good time here that I actually added three more weeks so this is the first of three reviews as I booked them separately. The host was really nice working with me and the associate that supports any household requests as well. Everything works perfectly, but the host associate was nice to come and anticipate the batteries on the smart lock would be running low and came and changed them along with leaving me extra snow melt, and a shovel after clearing the walkways. The house is well...
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

Amazing Lakefront Property

9.8 out of 10, Exceptional, (24)
"Absolutely beautiful house! Super clean! Superb setting! Very comfortable! Amazing view! Many amenities! Host very responsive and kind! The property manager quickly responded to our needs. My family and friends loved the spectacular experience and would definitely comeback! "
Amazing Lakefront Property

NEW-Another Fun Downtown Location 1st floor

2.0 star property
10.0 out of 10, Exceptional, (9)
"It was a nice quiet valuable time spent together .just what we needed for that very special memorable time. Thanks."
NEW-Another Fun Downtown Location 1st floor

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

10.0 out of 10, Exceptional, (9)
"My friends and I have stayed twice now at this house and have had the best time both times! It has everything we could need in the house and we can’t wait to be back again!"
The price is AED 2,204
AED 3,133 total
includes taxes & fees
23 Feb - 24 Feb
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

Island Vibes Home

9.8 out of 10, Exceptional, (13)
"House was just as described. Clean and well stocked. Communication and instructions were clear. Great location. "
Island Vibes Home

NEW 5Bed Close to Bloomfield Center & Golf Courses

2.0 star property
10.0 out of 10, Exceptional, (2)
"Omg i dont even know where to start but this property was phenomenal love it i would recommend a million times are more all im ask since this a newly released property plz take care of it like i did so otheres can have our experience clean after ur self if u can but quite spacious parking great nth to worry about 3 to 5 mins from most convenient places "
The price is AED 979
AED 2,424 total
includes taxes & fees
23 Feb - 24 Feb
NEW 5Bed Close to Bloomfield Center & Golf Courses

Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

10.0 out of 10, Exceptional, (42)
"This property is beautiful and the house is spacious and well equipped for a wonderful stay. The host was attentive and easy to contact when it was necessary. Such a fantastic choice for a stay in a delightful town. "
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

Near Yale with Game Room

The price is AED 1,969
AED 4,180 total
includes taxes & fees
23 Feb - 24 Feb
Near Yale with Game Room

Family Stays: Middletown, CT

10.0 out of 10, Exceptional, (2)
"We came to stay at Gilbert’s for a quick ski weekend at Powder Ridge. Gilbert was incredibly gracious and accommodating. He was very easy to communicate with, and really went out of his way to make us feel at home. The location is a little loud at night/early morning, as it is very close to a main road. But the property itself was exactly as described. Clean, comfortable, and very welcoming. "
The price is AED 342
AED 656 total
includes taxes & fees
23 Feb - 24 Feb
Family Stays: Middletown, CT

Beautiful 3BR, Rare Find, Clean & Guest Favorite

2.0 star property
10.0 out of 10, Exceptional, (2)
"Nice clean 3 bedroom that was as described. It was a short drive to downtown West Hartford."
The price is AED 481
AED 1,090 total
includes taxes & fees
3 Mar - 4 Mar
Beautiful 3BR, Rare Find, Clean & Guest Favorite

Enjoy a taste of New England in Historic Guilford Ct

10.0 out of 10, Exceptional, (9)
"Wonderful property combining original details with modern amenities. Well located near the town green and shops. We would definitely stay here again."
Enjoy a taste of New England in Historic Guilford Ct

Ranch style living at its best with country garden & patio!

9.6 out of 10, Exceptional, (8)
"Host worked with me due to larger dog. Very accurate instructions and all amenities were very good. Will stay here again"
Ranch style living at its best with country garden & patio!

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

10.0 out of 10, Exceptional, (25)
"The house is an architectural gem with plenty of space for the family. We enjoyed the fireplace in the evenings."
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

9.8 out of 10, Exceptional, (26)
"When my hometown sib couldn't host, we rented here and had our family Thanksgiving! It was great!"
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Waterfront House with picture-perfect views from all 3 levels.

9.6 out of 10, Exceptional, (78)
"Hosts were great with easy and quick communication! House was very clean and everything is clearly labeled. "
Waterfront House with picture-perfect views from all 3 levels.

Blue Back Bungalow

2.0 star property
9.8 out of 10, Exceptional, (9)
"Thank you so much for the amazing stay!!!! The place is beautiful, very clean and cosy! True Jem of West Hartford! We were here for my nieces wedding and felt very comfortable! Thank you for the wonderful TV set, amazing furniture, blow dryer and decorations! Everything in the house set up well and with love."
The price is AED 459
AED 1,413 total
includes taxes & fees
16 Mar - 17 Mar
Blue Back Bungalow

Spacious 5-bedroom, 6 bath vacation home just 30 min drive to beaches and casino

10.0 out of 10, Exceptional, (33)
"Spacious, full stocked, amenity filled home with enough room for family members to gather and/or spread out.The game room is perfect for all ages with a variety of choices for your competitive play. Grocery/liquor store and Gillette Castle State Park are minutes away.Beautiful area. "
Spacious 5-bedroom, 6 bath vacation home just 30 min drive to beaches and casino

Spacious 18th Century Victorian Mansion - Sleep 16+ Large Group

10.0 out of 10, Exceptional, (1)
"We had a lovely family gathering with 14 adults and a toddler - the house was perfect for a large family meal and had room for everyone. Lots of games, a pool table, and electric fireplace were great additions. Rick was very helpful and easy to communicate with. Convenient on site parking. As stated in listing, the bedrooms are on 2nd and 3rd floor, with grand/tall staircases. Overall it was a great place for our family to celebrate together!"
The price is AED 3,526
AED 6,220 total
includes taxes & fees
23 Feb - 24 Feb
Spacious 18th Century Victorian Mansion - Sleep 16+ Large Group

Storybook Cottage

10.0 out of 10, Exceptional, (1)
"Very charming property, accurate description per listing. Very clean and overall a great stay."
Storybook Cottage
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

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (6)
"I loved this escape from reality. This was a very quiet romantic getaway for Valentine’s Day. The place was very clean and had everything we needed from a fully equipped small kitchen to everything outdoors we would need for a campfire and making s’mores. I loved this place and can’t wait to come back for another romantic getaway."
Postcard Cabins Machimoodus

Waterfront House with picture-perfect views from all 3 levels.

9.6 out of 10, Exceptional, (78)
"Hosts were great with easy and quick communication! House was very clean and everything is clearly labeled. "
Waterfront House with picture-perfect views from all 3 levels.

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

9.0 out of 10, Wonderful, (86)
"Very cute ranch in a lovely neighborhood. Good location for access to area sites like Hammonasset Beach, Chamard Vineyard, and the Water's Edge. Not truly a "water's view", but the house had all the amenities needed for a fun stay! "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
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.