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 cabin with a dining table set for two, a bicycle, and a small porch area.

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, (192 reviews)
"ABSOLUTELY BEAUTIFUL AND SERENE STAY . WE REALLY ENJOYED OUR STAY !"
United States
Melissa
The price is €168
includes taxes & fees
30 Sept - 1 Oct
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
10.0 out of 10, Exceptional, (3 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 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.

3. 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, (37 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 €230
includes taxes & fees
19 Oct - 20 Oct
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A wooden deck with chairs overlooking a calm lake surrounded by autumn foliage.

4. #24 Serenity A Lakefront Cottage Retreat

#24 Serenity A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (25 reviews)
"It was great "
United States
Rodrigo C.
The price is €299
includes taxes & fees
28 Sept - 29 Sept
#24 Serenity A Lakefront Cottage Retreat
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

5. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (60 reviews)
"We enjoyed our stay"
United States
JM B.
The price is €208
includes taxes & fees
19 Oct - 20 Oct
1-bedroom cottage with Grove Beach 🏖️ access.
A large, white, multi-story building with a prominent tower and a flag on top.

6. 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
27 Oct - 28 Oct
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.

7. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (6 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is €253
includes taxes & fees
28 Sept - 29 Sept
2BR Apartment Near Wesleyan 102

8. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (31 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
The price is €229
includes taxes & fees
29 Sept - 30 Sept
Family Stays: Middletown, CT
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

9. 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, (13 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is €404
includes taxes & fees
27 Sept - 28 Sept
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
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, (28 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is €269
includes taxes & fees
8 Oct - 9 Oct
The gardners Cottage 1 mile from long Island Sound - pet friendly
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

11. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, Wonderful, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is €412
includes taxes & fees
28 Sept - 29 Sept
Adorable Cottage, 5 min walk to water & town
A beach with waves, a clear sky, and a sandy shore.

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 €273
includes taxes & fees
29 Sept - 30 Sept
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
A modern kitchen with dark cabinetry, a marble countertop, and a dining area with a table and chairs.

13. 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.
The price is €279
includes taxes & fees
6 Oct - 7 Oct
3 BR Apartment Near Wesleyan 201
A dining area with a wooden table, white chairs, a checkered tablecloth, a vase with flowers, and a decorative ceiling light.

14. 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)
"Great host and property"
United States
Kevin K.
The price is €461
includes taxes & fees
27 Sept - 28 Sept
Adorable Cottage with Cottage porch, walk to water & town
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 €489
includes taxes & fees
28 Sept - 29 Sept
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A modern living room with a sofa, a dining table, and a massage chair.

16. #29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.0 out of 10, Wonderful, (7 reviews)
"Great place! "
United States
Gail R.
The price is €437
includes taxes & fees
7 Oct - 8 Oct
#29 - Modern 5 Bedroom/2 Bath
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

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

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (2 reviews)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is €584
includes taxes & fees
20 Oct - 21 Oct
Beachside Bliss w/ Game Room, Gym & Golf Green
A two-story house with a front porch, a garage, and a well-maintained lawn.

18. Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Middletown
9.6 out of 10, Exceptional, (19 reviews)
"The house was exactly what we were looking for, for a weekend away. Will surely book again, thank you!"
United States
Lee S.
The price is €722
includes taxes & fees
30 Sept - 1 Oct
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
A modern kitchen with a central island, bar stools, and pendant lighting.

19. 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, (32 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 €914
includes taxes & fees
28 Sept - 29 Sept
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
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.

20. Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
The price is €814
includes taxes & fees
27 Sept - 28 Sept
Conference Room Rental no sleeping arrangements
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

New Haven Hotel

New Haven Hotel

8/10 Good
"The staff members at check-in & check-out were warmly professional and attentive. What a gorgeous & spacious living room area with appealing decor. The breakfast options were fantastic for self-serve options. The room was immaculate. Two points that led me to rate it a 4.7 out of 5 = the extremely hard bed & non-working light & electric fixtures on the side of the bed by the window."
Maria Luisa 1-night trip
Posted 9 hours ago
New Haven Hotel

Find out more about Middlesex County

Holiday Homes in Middlesex County

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