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Middletown Holiday Rentals

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Holiday Rentals in Middletown

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (5)
"Loved how tranquil this site is. Was great to disconnect in nature. "
The price is AU$163
includes taxes & fees
4 Mar - 5 Mar
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.

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!

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 AU$541
includes taxes & fees
18 Feb - 19 Feb
Blue Back Bungalow

COZY Maple Tree Cabin - Romantic or family getaway. Private - Warm and Cozy!

10.0 out of 10, Exceptional, (26)
"We were in awe of how cool this cabin is, everyone kept saying, “ It’s like a Hallmark Christmas movie”. It couldn’t have been more perfect for our family. The 8yr old twin boys loved the air hockey table and it was great having that space upstairs for them to enjoy movies and games too. We had a great Christmas dinner and had all the amenities, perfect amount of seating. We tried s’mores at the fire pit, but made them quickly and ran in because it was 15 but we still got in another great...
The price is AU$1,183
includes taxes & fees
24 Feb - 25 Feb
COZY Maple Tree Cabin - Romantic or family getaway. Private - Warm and Cozy!

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

9.8 out of 10, Exceptional, (107)
"Cute place, very clean"
The price is AU$801
includes taxes & fees
17 Feb - 18 Feb
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

10.0 out of 10, Exceptional, (59)
"Our family ranged in ages from 13 to 96. We were 12 people for a couple days and then 10. We all had a marvelous time and my mom just can’t stop talking about how beautiful the view and the antique furniture was. It was difficult for that many people only having two bathrooms, but we made it work. We did run out of hot water so we learned to scatter showers when possible. The view is amazing and the location was wonderful for us. I can’t say enough, how accommodating our hostess was. We told her...
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

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

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!

Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family

10.0 out of 10, Exceptional, (14)
"This rental is so unique with the 2 sides, and was absolutely perfect for our wedding weekend. We had the groom’s friends staying on one side, and my friends staying on the other side. The two sides are connected through the sunroom and the backyard space is great which made bringing the whole group together so easy. The setup was also perfect for me to get ready on my own separate side the day of the wedding so that my now husband wouldn’t see me. The decor and cleanliness of the house were...
Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family

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

Historic Essex Home w/ Large Yard Near Downtown!

10.0 out of 10, Exceptional, (44)
"Everything was great! Perfect writing retreat"
Historic Essex Home w/ Large Yard Near Downtown!

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

1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

9.0 out of 10, Wonderful, (22)
"Spent a weekend in this cottage while attending an event for my daughter. Very cozy and comfortable. Host was great, with excellent communication. Renovations are taking place in adjacent units, however it did not impact my stay. Highly recommend. "
The price is AU$277
includes taxes & fees
17 Feb - 18 Feb
1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

Waterfront Cottage in Branford

10.0 out of 10, Exceptional, (90)
"House is beautiful and the view even better. On the waters edge and very quiet grandkids were occupied and very happy "
Waterfront Cottage in Branford

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Tranquil 3-bedroom house with additional full-size sofa bed in Hartford

The price is AU$602
includes taxes & fees
10 Mar - 11 Mar
Tranquil 3-bedroom house with additional full-size sofa bed in Hartford

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

Beach front property steps from Long Island Sound!

10.0 out of 10, Exceptional, (15)
"This is our second year at The Salty Seahorse! The property is clean and well maintained. The beach is perfect. Great location!"
Beach front property steps from Long Island Sound!

Charming Westbrook Cottage, Steps to Private Beach

10.0 out of 10, Exceptional, (2)
"Cozy cottage, good location, nice access to the Sound."
Charming Westbrook Cottage, Steps to Private 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.
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Other types of properties in Middletown you may be interested in

Inn at Middletown

3.5 star property
9.0 out of 10, Wonderful, (445)
"There were lots of restaurants and shopping nearby and the route was easily accessible. Staff was friendly and helpful with questions we asked. "
The price is AU$330
includes taxes & fees
17 Feb - 18 Feb
Inn at Middletown

New Haven Hotel

3.5 star property
8.8 out of 10, Excellent, (1458)
"Great location close to Yale. Property was clean, room was comfortable and free adjacent parking was nice."
The price is AU$214
includes taxes & fees
16 Mar - 17 Mar
New Haven Hotel

Omni New Haven Hotel at Yale

4.0 star property
8.2 out of 10, Very good, (1005)
"Staff was welcoming and readily answered any questions or concerns."
The price is AU$274
includes taxes & fees
2 Mar - 3 Mar
Omni New Haven Hotel at Yale
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.

Frequently asked questions

Are there holiday rentals in Middletown?

Yes, there are holiday rentals in Middletown close to Kidcity Children's Museum, or you can select a more secluded option if you're looking for a relaxing stay. Middletown is known for its entertainment choices and festivals. Make sure you have time to check out the basketball games and university setting during your trip.

What are some of the best holiday rentals that Middletown has to offer?

Cozy Westbrook Vacation Rental - Walk to Beach!: This holiday home rental outside of Middletown is located near the beach, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Middletown?

With 8 Expedia holiday rentals, you're guaranteed to find just the right place for your Middletown stay.

What’s there to see and do in Middletown?

Family-friendly attractions include Kidcity Children's Museum and Van Vleck Observatory, whereas Connecticut River and General Mansfield House are a couple of great spots to enjoy the outdoors. Other places in town to visit include Wadsworth Mansion and Smith Park.

What’s a holiday rental in Middletown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middletown. Holiday rentals feature amenities like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips.