A coastal town with a lighthouse, houses, and a river.

Holiday Rentals in Middlesex County

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Our top choices for Middlesex County holiday rentals

A glass enclosure with a view of a forest interior, including a bed and a small table with items.

1. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (222 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
The price is €171
includes taxes & fees
9 Dec - 10 Dec
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A modern kitchen with a central island, white cabinetry, stainless steel appliances, and a wooden floor.

2. 2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
9.6 out of 10, Exceptional, (4 reviews)
"The living quarters was clean, no bugs, essentials provided (except laundry detergent and hair dryer), quiet residence, muddy parking lot, safe neighborhood, great communication and ease of parking and entry. "
United States
Joanne L.
2BR Apartment Near Wesleyan 301
A large, white, multi-story building with a prominent tower and a flag on top.

3. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (43 reviews)
"Very convenient location with good parking"
United States
Anonymous traveller
The price is €221
includes taxes & fees
30 Nov - 1 Dec
Walk To Goodspeed Opera House!
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

4. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
8.8 out of 10, Excellent, (8 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is €212
includes taxes & fees
11 Nov - 12 Nov
2BR Apartment Near Wesleyan 102
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a coffee table. There is a kitchen in the background with white cabinets and a wooden countertop.

5. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (40 reviews)
"We had a great stay, very clean and cozy! Our host was very nice and responsive. Great location, would definitely recommend!!!"
United States
Kristy C.
The price is €228
includes taxes & fees
17 Nov - 18 Nov
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A modern kitchen with dark cabinetry, a marble countertop, and a dining area with a table and chairs.

6. 3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Clean apartment plenty of parking"
United States
Rebecca P.
3 BR Apartment Near Wesleyan 201
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

7. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.8 out of 10, Exceptional, (66 reviews)
"Cozy vrbo with a great location to the beach, outlets shops and excellent restaurants!"
United States
Marcy C.
1-bedroom cottage with Grove Beach 🏖️ access.
A room with a patterned rug, a door leading to a kitchen, and a window with blinds.

8. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (34 reviews)
"Gilbert is an amazing host! I highly recommend staying here if you are visiting Middletown."
United States
Audrey F.
The price is €223
includes taxes & fees
16 Nov - 17 Nov
Family Stays: Middletown, CT
A two-story house with a front porch, large windows, and a well-maintained lawn.

9. New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Durham
10.0 out of 10, Exceptional, (35 reviews)
"This was an amazing home that exceeded our expectations- it was clean, comfortable, and in such a beautiful setting! A great place for our family to stay together during a college graduation trip! We would certainly come back again!"
United States
Iris F.
The price is €1,030
includes taxes & fees
11 Nov - 12 Nov
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

10. The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (32 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The price is €308
includes taxes & fees
11 Nov - 12 Nov
The gardners Cottage 1 mile from long Island Sound - pet friendly
A modern office space with a sofa, two round tables, and a coffee table. There are chairs around the tables, a rug on the floor, and a door in the background.

11. Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
The price is €881
includes taxes & fees
24 Nov - 25 Nov
Conference Room Rental no sleeping arrangements
A modern loft apartment with a dining area, kitchenette, and a cozy seating area.

12. Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Westbrook Center
10.0 out of 10, Exceptional, (1 review)
"Able to walk to all the nearby restaurants with this location, including the beach. Very clean rooms with 2 TVs and controllable AC. Would definitely visit here again."
United States
Mason T.
The price is €348
includes taxes & fees
10 Dec - 11 Dec
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
A modern kitchen with a granite island, stainless steel appliances, and a bar area with bar stools.

13. Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (4 reviews)
"Very lovely home! We very much enjoyed our stay and hope to be back again!"
United States
Morgan M.
The price is €544
includes taxes & fees
1 Dec - 2 Dec
Beachside Bliss w/ Game Room, Gym & Golf Green
An outdoor kitchen area with a stone fireplace, grill, and built-in refrigerator.

14. Cozy 1 bedroom private farmhouse apartment

Cozy 1 bedroom private farmhouse apartment
Durham
The price is €259
includes taxes & fees
24 Nov - 25 Nov
Cozy 1 bedroom private farmhouse apartment
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

15. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (140 reviews)
"This house comfortably sleeps a lot of guests and has a well equipped kitchen. Everything was very clean. The hosts were very easy to communicate with and very helpful."
United States
Alexis L.
The price is €488
includes taxes & fees
16 Nov - 17 Nov
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A modern living room with a large TV, white cabinetry, and a view of the outdoors.

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

Charming beach home, complete with pool & cozy guest house!
Clinton
9.8 out of 10, Exceptional, (56 reviews)
"Beautiful, open and clean. Perfect for a family stay!"
United States
Juliana A.
The price is €1,062
includes taxes & fees
12 Nov - 13 Nov
Charming beach home, complete with pool & cozy guest house!
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

17. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
10.0 out of 10, Exceptional, (15 reviews)
"Cute little house with excellent amenities. Perfect for our cousins getaway!"
United States
Karol T.
The price is €410
includes taxes & fees
15 Nov - 16 Nov
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
A dining area with a wooden table, white chairs, a checkered tablecloth, a vase with flowers, and a decorative ceiling light.

18. Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
9.0 out of 10, Wonderful, (8 reviews)
"Very clean and comfortable"
United States
Francine F.
Adorable Cottage with Cottage porch, walk to water & town
A living room with stone walls, a fireplace, and a seating area with a sofa and armchairs.

19. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Getaway-Near Beaches, Train & Shoreline
Westbrook Center
The price is €393
includes taxes & fees
11 Dec - 12 Dec
Westbrook Getaway-Near Beaches, Train & Shoreline
A compact kitchen with white cabinets, a built-in oven, and a dining table with chairs.

20. Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101
Washington Street Historic District
7.2 out of 10, Good, (5 reviews)
"Very clean. No frills."
United States
Kristoph
The price is €236
includes taxes & fees
11 Nov - 12 Nov
Private Apt in Middletown-Wesleyan 101
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 Middlesex County Hotel Reviews

Two Trees Inn

Two Trees Inn

8/10 Good
"It was a very convenient spot and much cheaper than the casino is normally charging, especially on a weekend. We were able to see a show on Friday night and stay for two nights for the price of what it would’ve cost to stay one night at the casino."
Renee 2-night trip
Posted less than an hour ago
Two Trees Inn

Find out more about Middlesex County

Holiday Homes in Middlesex County

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