Holiday Rentals in Middlesex County

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Featured Holiday Rentals in Middlesex County

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (79)
"Very nice cabins "
United States
Jairo
The price is €189
includes taxes & fees
12 Nov - 13 Nov
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Charming New England Tiny Home in Cromwell, CT
The price is €174
includes taxes & fees
6 Nov - 7 Nov
Charming New England Tiny Home in Cromwell, CT
Family Stays: Middletown, CT
10.0 out of 10, Exceptional, (17)
"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."
United States
Michael H.
The price is €199
includes taxes & fees
12 Nov - 13 Nov
Family Stays: Middletown, CT
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
10.0 out of 10, Exceptional, (51)
"Amazing property, we loved everything about it, highly recommended, will stay again "
United States
Rick
The price is €698
includes taxes & fees
20 Nov - 21 Nov
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Walk To Goodspeed Opera House!
9.4 out of 10, Exceptional, (34)
"The place was spotless and comfortable. Would highly recommend!"
United States
Jeanne Y.
The price is €246
includes taxes & fees
11 Nov - 12 Nov
Walk To Goodspeed Opera House!
Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
The price is €417
includes taxes & fees
11 Nov - 12 Nov
Beachside Bliss w/ Game Room, Gym & Golf Green
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
10.0 out of 10, Exceptional, (21)
"Beautiful house, like new, on a quiet street. Exactly as described, very comfortable. "
United States
Doug F.
The price is €785
includes taxes & fees
16 Nov - 17 Nov
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Peace Barn in the heart of the CT River Valley
2.0 star property
8.6 out of 10, Excellent, (4)
"The grounds were beautiful Everything else for me and my family’ was awful and should not be rented as a vrbo. Lots of bugs. The upstairs bathroom had no water pressure or hot water. The upstairs bedroom window and screen were duct taped shut. The kitchen was a mishmash of things that didn’t work. The house did smell of mold. The only thing this property has to offer is the lake and the land the lodging was terrible and not at all comfortable. And the lights were terrible, if you could even...
United States
Cindy G.
The price is €635
includes taxes & fees
19 Nov - 20 Nov
Peace Barn in the heart of the CT River Valley
Conference Room Rental no sleeping arrangements
The price is €819
includes taxes & fees
6 Nov - 7 Nov
Conference Room Rental no sleeping arrangements
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
10.0 out of 10, Exceptional, (34)
"Enjoyed our stay"
United States
Nicole L.
The price is €1,052
includes taxes & fees
27 Nov - 28 Nov
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Spacious Lakefront Home|Bikes|Hot Tub| Kayak|Group
The price is €752
includes taxes & fees
19 Nov - 20 Nov
Spacious Lakefront Home|Bikes|Hot Tub| Kayak|Group
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
10.0 out of 10, Exceptional, (26)
"The property was excellent. Quiet, comfortable and roomy. The bed was really comfortable and we have already booked to come back in July. The personal touches were wonderful. We loved the place, perfect been for 1 or 2 people."
United States
Victoria S.
The price is €228
includes taxes & fees
12 Nov - 13 Nov
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Apartment in Middletown-Wesleyan102
2.0 star property
The price is €286
includes taxes & fees
1 Dec - 2 Dec
Apartment in Middletown-Wesleyan102
1-bedroom cottage with Grove Beach 🏖️ access.
9.2 out of 10, Wonderful, (36)
"Host was very friendly and accommodating"
United States
Monika M.
The price is €180
includes taxes & fees
7 Nov - 8 Nov
1-bedroom cottage with Grove Beach 🏖️ access.
Cozy Guest Suite in Historic Home
The price is €191
includes taxes & fees
9 Nov - 10 Nov
Cozy Guest Suite in Historic Home
Shoreline Oasis
9.2 out of 10, Wonderful, (7)
"Cute apartment in a house, separate from the hosts space downstairs. Clean and walking distance to some great harbor-front restaurants. 1 bed and 2 couches (no pull-out couch)"
United States
Molly H.
The price is €231
includes taxes & fees
6 Nov - 7 Nov
Shoreline Oasis
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
9.6 out of 10, Exceptional, (38)
"Nicely decorated and clean. "
United States
Lauren
The price is €454
includes taxes & fees
6 Nov - 7 Nov
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
9.6 out of 10, Exceptional, (133)
"We thoroughly enjoyed our stay...the historic home was a perfect New England getaway for our group of women."
United States
Shari M.
The price is €458
includes taxes & fees
6 Nov - 7 Nov
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Private Apt in Middletown-Wesleyan
6.0 out of 10, (2)
"The apartment was exactly what we needed to rest between events at Wesleyan. Good communication, fixed an air conditioner and added one prior to our arrival (and it was very very hot. So it was appreciated."
United States
Carolyn O.
Private Apt in Middletown-Wesleyan
3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay
6.6 out of 10, (4)
"Nice place"
United States
Jousette C.
The price is €204
includes taxes & fees
11 Nov - 12 Nov
3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Middlesex County Hotel Reviews

Find out more about Middlesex County

Holiday Homes in Middlesex County

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

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

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