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

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, (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! "
The price is AED 551
AED 1,591 total
includes taxes & fees
23 Dec - 24 Dec
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Charming beach home, complete with pool & cozy guest house!
Exterior

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!
Family Gem on Dyer Street

Family Gem on Dyer Street

10.0 out of 10, Exceptional, (2)
"Needed a place to stay for the night and it was just the perfect spot. The house was just as it seemed online and it was a lot bigger than I expected. Everything was really nice and the host was super nice and very easy to communicate with. Would 100% recommend to others for their next stay."
The price is AED 731
AED 1,458 total
includes taxes & fees
16 Jan - 17 January 2025
Family Gem on Dyer Street
15mins to Hartford, Home in Manchester w/ King Bed
Exterior

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 942
AED 1,675 total
includes taxes & fees
22 Dec - 23 Dec
15mins to Hartford, Home in Manchester w/ King Bed
Spacious 5-bedroom, 6 bath vacation home just 5 min drive to Connecticut River
Back Patio-Pool, Hot tub, Fireplace, firepit, Bar & TV, Bathroom, Outdoor Shower

Spacious 5-bedroom, 6 bath vacation home just 5 min drive to Connecticut River

10.0 out of 10, Exceptional, (31)
"We stayed for our annual Columbus Day weekend away with a group of 9 friends. The house was very comfortable and we had plenty of space. We really enjoyed the game room in the evenings - all the games were in excellent condition and everything was in working order (which has not usually been the case at other vacation rentals we have been to). We were lucky enough to have beatiful fall weather all weekend, so we could enjoy the lovely back yard. We made use of the gas grill, watch a playoff game...
Spacious 5-bedroom, 6 bath vacation home just 5 min drive to Connecticut River
Island Vibes Home
Living area

Island Vibes Home

10.0 out of 10, Exceptional, (10)
"Such a perfect space for us. Home was spotless! We had a wedding in Hartford, three bedrooms worked out perfectly two bathrooms everyone had plenty of space. Beautiful kitchen and amenities. We would stay here again in a heartbeat. Wish we could’ve stayed longer"
Island Vibes Home
Enjoy a taste of New England in Historic Guilford Ct
Property grounds

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
146 Raymond · Prime West Hartford Center: Timeless Charm
kitchen

146 Raymond · Prime West Hartford Center: Timeless Charm

10.0 out of 10, Exceptional, (10)
"Great old West Hartford home. Very convenient to Center activities for us this weekend. Owner great to deal with. Highly recommended."
146 Raymond · Prime West Hartford Center: Timeless Charm
Ranch style living at its best with country garden & patio!
Room

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 8 beds Gaming Room
Exterior

Near Yale 8 beds Gaming Room

The price is AED 1,969
AED 3,968 total
includes taxes & fees
20 Jan - 21 January 2025
Near Yale 8 beds Gaming Room
Luxe Lake House in Connecticut
Sun Room

Luxe Lake House in Connecticut

10.0 out of 10, Exceptional, (1)
The price is AED 1,118
AED 3,439 total
includes taxes & fees
20 Jan - 21 January 2025
Luxe Lake House in Connecticut
Cozy 4 Bedroom West Hartford House
Living area

Cozy 4 Bedroom West Hartford House

2.0 star property
Cozy 4 Bedroom West Hartford House
Beautiful 3BR, Rare Find, Clean & Guest Favorite
Living area

Beautiful 3BR, Rare Find, Clean & Guest Favorite

2.0 star property
10.0 out of 10, Exceptional, (1)
"Enjoyed one night in this 3Br property. It was comfortable, secure and easy to locate. Great parking, kitchen, tv and wash/dry facilities. Would recommend."
The price is AED 481
AED 1,093 total
includes taxes & fees
20 Jan - 21 January 2025
Beautiful 3BR, Rare Find, Clean & Guest Favorite
Spacious, quiet suburban getaway in Madison. 15 min from beach & hiking trails!
Exterior

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!
Cozy Coastal Getaway
Private kitchen

Cozy Coastal Getaway

2.0 star property
10.0 out of 10, Exceptional, (1)
"My daughter and I recently spent four wonderful nights at this incredible home, and we couldn't have been happier. It was cozy, impeccably clean, and the hosts were very responsive. The location was perfect—just halfway to the water and two blocks from the charming Guilford Green. It’s a beautiful area, perfect for walking or running. The hosts went above and beyond by providing thoughtful touches like B&BW toiletries, high-quality linens, coffee, and essential cooking ingredients. We truly...
Cozy Coastal Getaway
Beautiful House in Great Neighborhood - Rare Find
Exterior

Beautiful House in Great Neighborhood - Rare Find

2.0 star property
The price is AED 280
AED 825 total
includes taxes & fees
16 Jan - 17 January 2025
Beautiful House in Great Neighborhood - Rare Find
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Dining area overlooking private beachfront

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!
Exterior image

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

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

9.6 out of 10, Exceptional, (11)
"Our visit at this VRBO was almost excellent… the only issue we had was with theTVs. We could not get the TVs in the bedroom to work. Cleanliness was exceptional! Availability of food/meal supplies was great. It was nice that there was ice already made for us. The towel and wash cloths were fluffy and absorbent. The queen bed and pillows were very comfortable. We cannot say there was anything that did not meet expectations! Anyone would be comfortable there. We would book again. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Waterfront House with picture-perfect views from all 3 levels.
Third level patio, off of bedroom with queen bed and twin bed with trundle.

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

9.6 out of 10, Exceptional, (76)
"Third time visitors so we obviously enjoy this property. Very nice/comfortable house in great location. "
Waterfront House with picture-perfect views from all 3 levels.
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
Spacious 5-bedroom, 6 bath vacation home just 5 min drive to Connecticut River
Back Patio-Pool, Hot tub, Fireplace, firepit, Bar & TV, Bathroom, Outdoor Shower

Spacious 5-bedroom, 6 bath vacation home just 5 min drive to Connecticut River

10.0 out of 10, Exceptional, (31)
"We stayed for our annual Columbus Day weekend away with a group of 9 friends. The house was very comfortable and we had plenty of space. We really enjoyed the game room in the evenings - all the games were in excellent condition and everything was in working order (which has not usually been the case at other vacation rentals we have been to). We were lucky enough to have beatiful fall weather all weekend, so we could enjoy the lovely back yard. We made use of the gas grill, watch a playoff game...
Spacious 5-bedroom, 6 bath vacation home just 5 min drive to Connecticut River
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.