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Compare 304 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!

The Santiago in Science Park at Yale New Haven

8.0 out of 10, Very Good, (5)
"Stay was great. You are within a longish walk or very short drive of all the good stuff in and around New Haven. We had a little mix up with the bedding left by the laundry service but hosts fixed it right away. Unique unit with some fun character. Would stay there again. "
The price is AED 364
AED 661 total
includes taxes & fees
3 Feb - 4 Feb
The Santiago in Science Park at Yale New Haven

15mins to Hartford, Home in Manchester w/ King Bed

2.0 star property
7.0 out of 10, Good, (2)
"We stay in rental all the time. This was definitely the worst that we have ever seen. There was no booklet of information left to give you instructions for the house. There were no labels on switches, instructions on how to use the fireplace, photograph of the supplies in the kitchen were not the same as what you Experienced. Made it very difficult to cook, so we just didn’t. The pots and pans were old and scratched, and not the kind of thing that anybody should be using and they should be...
The price is AED 481
AED 1,093 total
includes taxes & fees
3 Feb - 4 Feb
15mins to Hartford, Home in Manchester w/ King Bed

Spacious 5-bedroom, 6 bath vacation home just 30 min drive to casinos

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 casinos

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 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
20 Jan - 21 Jan
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

Island Vibes Home

10.0 out of 10, Exceptional, (12)
"House was just as described. Clean and well stocked. Communication and instructions were clear. Great location. "
Island Vibes Home

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

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.

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!

Near Yale with Game Room

The price is AED 1,969
AED 4,205 total
includes taxes & fees
20 Jan - 21 Jan
Near Yale with Game Room

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 1,093 total
includes taxes & fees
20 Jan - 21 Jan
Beautiful 3BR, Rare Find, Clean & Guest Favorite

Spacious, quiet suburban getaway in Madison. 15 min from beach & hiking trails!

2.0 star property
10.0 out of 10, Exceptional, (6)
"We had an absolute fantastic time staying at this place. My son was got married at the Beech Tree Cottages (also was the perfect wedding venue) in Madison, Ct. about 15 minutes from the house which worked out perfectly for staying here. From start to finish, everything exceeded our expectations. The communication with Chase was smooth and prompt, making the booking process hassle free. Upon our arrival we were greeted with a welcome gift. The space was clean, modern and beautifully...
Spacious, quiet suburban getaway in Madison. 15 min from beach & hiking trails!

Family Stays: Middletown, CT

10.0 out of 10, Exceptional, (1)
"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 AED 404
AED 728 total
includes taxes & fees
22 Jan - 23 Jan
Family Stays: Middletown, CT

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

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

10.0 out of 10, Exceptional, (24)
"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!

Waterfront Beach House

9.6 out of 10, Exceptional, (42)
"The property is nicely located on the water and convenient to many attractions. "
Waterfront Beach House

Charming Coastal Retreat Steps from the Beach!

9.8 out of 10, Exceptional, (31)
"The house was perfect for our multi generation gathering, spacious enough for all. The kitchen was well equipped for our cooking needs. The beds very comfortable. Would highly recommend it!"
Charming Coastal Retreat Steps from the Beach!

Charming beach home, complete with pool & cozy guest house!

9.6 out of 10, Exceptional, (23)
"Wonderful property. Plenty of room for 7 adults. Would definitely stay there again. "
Charming beach home, complete with pool & cozy guest house!

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
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

8.4 out of 10, Very Good, (17)
"I stayed for about two days and nights and had a great experience. The house was clean, everything we needed was easy to find, the only thing was that the shower was a little clogged. Overall, it was a great experience!!"
Cozy newly remodeled home close to major amenities in Connecticut a

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!

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (106)
"Wonderful place to spend time with the family in this cozy cottage. Would love to come back in the summer to enjoy the beach. "
The price is AED 793
AED 1,850 total
includes taxes & fees
20 Jan - 21 Jan
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.