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Middletown Holiday Rentals

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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Holiday Rentals in Middletown

Exterior
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Cabin in East Haddam

2.0 star property
9.6 out of 10, Exceptional, (82)
"Very nice cabins "
United States
Jairo
The price is HK$787
HK$1,262 total
includes taxes & fees
1 Dec - 2 Dec
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Iron/ironing board, WiFi, bed sheets
Lux Boutique Large Private LOFT Pratt St Hartford

Apartment in Downtown Hartford

8.4 out of 10, Very good, (23)
"Very clean and spacious! Loved all the amenities. Room itself was a bit echoey, but nice and quiet."
United States
Kiara
The price is HK$778
HK$1,184 total
includes taxes & fees
1 Dec - 2 Dec
Lux Boutique Large Private LOFT Pratt St Hartford
Microwave
Cozy apartment in charming Hartford with AC, WiFi

Apartment in Downtown Hartford

9.0 out of 10, Wonderful, (7)
"Very nice for one night"
United States
Jack
The price is HK$778
HK$1,184 total
includes taxes & fees
30 Nov - 1 Dec
Cozy apartment in charming Hartford with AC, WiFi
Fridge, microwave, oven, dishwasher
Large Charming Historic House close to Beaches

Holiday Home in Clinton

9.8 out of 10, Exceptional, (35)
"Great place and location. There was 8 of us and plenty of space and beds!"
United States
Sandy B.
Large Charming Historic House close to Beaches
Exterior
Charming Studio| Near Yale| Downtown New Haven

Apartment in Downtown New Haven

9.0 out of 10, Wonderful, (10)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
United States
Jason K.
The price is HK$731
HK$1,633 total
includes taxes & fees
30 Nov - 1 Dec
Charming Studio| Near Yale| Downtown New Haven
Fridge, microwave, oven, stovetop
Private Apartment in Berlin

Holiday Home in Berlin

2.0 star property
9.2 out of 10, Wonderful, (5)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
United States
Stacy B.
The price is HK$910
HK$2,457 total
includes taxes & fees
30 Nov - 1 Dec
Private Apartment in Berlin
Exterior
Shoreline Oasis

Apartment in Clinton

9.2 out of 10, Wonderful, (7)
"Everything was as advertised or better. Lovely quiet area near beautiful beaches and great restaurants. We had a terrific experience. "
United States
Tom S.
The price is HK$1,392
HK$2,019 total
includes taxes & fees
29 Nov - 30 Nov
Shoreline Oasis
Interior
Conference Room Rental no sleeping arrangements

Apartment in Main Street Historic District

The price is HK$5,598
HK$7,239 total
includes taxes & fees
28 Nov - 29 Nov
Conference Room Rental no sleeping arrangements
Dining
Coastal Holiday Retreat: Luxury Waterfront, Hot Tub & Private Beach

Holiday Home in Branford

10.0 out of 10, Exceptional, (71)
"Great family get together where we all were very comfortable. "
United States
Leanne B.
Coastal Holiday Retreat: Luxury Waterfront, Hot Tub & Private Beach
Smart TV
1-bedroom cottage with Grove Beach 🏖️ access.

Cottage in Clinton

9.2 out of 10, Wonderful, (36)
"Cottage itself clean, but sewage smell in bathroom. Surrounding property derelict motel with ongoing consruction. "
United States
michelle
The price is HK$476
HK$1,302 total
includes taxes & fees
1 Dec - 2 Dec
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Apartment in Madison

10.0 out of 10, Exceptional, (36)
"We had a wonderful time here!! "
United States
Leslie S.
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
4 bedrooms, iron/ironing board, free WiFi, bed sheets
Waterfront Cottage in Branford

Cottage in branford

10.0 out of 10, Exceptional, (97)
"Beautiful location "
United States
Anne d.
Waterfront Cottage in Branford
Fridge, microwave, oven, stovetop
New Cozy 2BR Stay New Haven Close to Yale

Apartment in East Rock

2.0 star property
7.4 out of 10, Good, (3)
"Place was great for family and having a washer and dryer was a big help. Place was super clean and comfortable "
United States
CHUCK C.
New Cozy 2BR Stay New Haven Close to Yale
WiFi, bed sheets
Totally Private Cozy studio in awesome Hartford with WiFi, AC

Apartment in Downtown Hartford

8.6 out of 10, Excellent, (11)
"Great!"
United States
Sahai S.
The price is HK$778
HK$1,184 total
includes taxes & fees
30 Nov - 1 Dec
Totally Private Cozy studio in awesome Hartford with WiFi, AC
Sun-loungers, beach towels
Waterfront Goodspeed airport 2-bedroom house with AC, WiFi

Holiday Home in East Haddam

2.0 star property
9.6 out of 10, Exceptional, (15)
"We had a great time. Looking forward to our next stay here!"
United States
Jacky P.
Waterfront Goodspeed airport 2-bedroom house with AC, WiFi
Dining
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Holiday Home in Old Saybrook

10.0 out of 10, Exceptional, (34)
"Enjoyed our stay"
United States
Nicole L.
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
TV
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Holiday Home in New Britain

10.0 out of 10, Exceptional, (7)
"The space was clean and light, great finishes. The home felt comfortable and was easy to find. Thank you for a wonderful weekend. "
United States
Lara S.
The price is HK$875
HK$1,916 total
includes taxes & fees
1 Dec - 2 Dec
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
Beach nearby, beach towels
Gorgeous 4BR Beach House with Private Beach Access.

Holiday Home in Pine Orchard

9.8 out of 10, Exceptional, (76)
"Nice property, thanks to the owners.Jackie"
United States
Jacqueline M.
Gorgeous 4BR Beach House with Private Beach Access.
Beach nearby
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

Holiday Home in Branford Center

9.2 out of 10, Wonderful, (19)
"This Carriage House is exactly as described. Wonderful location and setting, just steps away from Branford Point. Hope to visit again soon! "
United States
Terri L.
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Fridge, microwave, oven, stovetop
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking

Apartment in Downtown Hartford

9.0 out of 10, Wonderful, (2)
"The location is fabulous to the convention center is fabulous!"
United States
Anonymous traveller
The price is HK$1,120
HK$2,375 total
includes taxes & fees
29 Nov - 30 Nov
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking
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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Top Middletown Hotel Reviews

New Haven Hotel

New Haven Hotel

10/10 Excellent
"Easy check-in and courteous staff."
Laura 1-night trip
Posted 3 days ago
New Haven Hotel

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

  • View our selection of featured holiday rentals in Middletown
  • Use the map to find apartments and other holiday homes in the Middletown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middletown while they last

Look no further and take a look at our great range of rental properties in Middletown!

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?

Large Charming Historic House close to Beaches: This holiday home rental outside of Middletown is located near the beach, and has a patio, a garden and air conditioning to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and an oven, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Middletown?

With 11 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 Wadsworth Falls State Park are a couple of great spots to enjoy the outdoors. Other places in town to visit include Wadsworth Mansion and Artfarm.

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.