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

Search Holiday Rentals in Middlesex County

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Middlesex County Accommodation: Most Popular Cities to Stay

A rocky beach with large boulders and the ocean in the background.
Holiday RentalsHoliday Rentals

Old Saybrook

Old Saybrook

Our top choices for Middlesex County holiday rentals

View from property

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, (177 reviews)
"Great property for quiet and a nice getaway. Great little places to eat and shop in the surrounding towns."
United States
Frank
The price is £183
includes taxes & fees
10 Sept - 11 Sept
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
1 bedroom, desk, iron/ironing board, travel cot

2. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (51 reviews)
"We enjoyed our stay"
United States
JM B.
The price is £170
includes taxes & fees
8 Sept - 9 Sept
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV, fireplace, books, music library

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, (35 reviews)
"My son and I were here for two nights and had an excellent time. It was exactly as described and such a tastefully decorated and maintained place to stay. Would definitely stay here again if in the area!"
United States
Kate F.
The price is £194
includes taxes & fees
24 Aug - 25 Aug
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Property grounds

4. #24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"It was great "
United States
Rodrigo C.
The price is £306
includes taxes & fees
18 Aug - 19 Aug
#24 *Serenity* A Lakefront Cottage Retreat
Dining

5. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (4 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is £191
includes taxes & fees
13 Aug - 14 Aug
2BR Apartment Near Wesleyan 102
Coffee/tea maker, fridge, microwave, oven

6. 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.
The price is £210
includes taxes & fees
13 Aug - 14 Aug
2BR Apartment Near Wesleyan 301
Property grounds

7. Lakeview Carriage House with Spectacular Sunset Views

Lakeview Carriage House with Spectacular Sunset Views
Lake Pocotopaug
10.0 out of 10, Exceptional, (19 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is £233
includes taxes & fees
7 Sept - 8 Sept
Lakeview Carriage House with Spectacular Sunset Views
Exterior

8. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (40 reviews)
"Simple process, plenty of room, ample parking and no issues with noise from the business above. "
United States
Amber J.
The price is £210
includes taxes & fees
18 Aug - 19 Aug
Walk To Goodspeed Opera House!
Coffee/tea maker, fridge, microwave, oven

9. 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, (26 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is £259
includes taxes & fees
1 Sept - 2 Sept
The gardners Cottage 1 mile from long Island Sound - pet friendly
Smart TV

10. #29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.4 out of 10, Exceptional, (6 reviews)
"Great place! "
United States
Gail R.
The price is £352
includes taxes & fees
19 Aug - 20 Aug
#29 - Modern 5 Bedroom/2 Bath
Interior

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

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (16 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is £312
includes taxes & fees
13 Aug - 14 Aug
Adorable Cottage, 5 min walk to water & town
Dining

12. 3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
10.0 out of 10, Exceptional, (1 review)
"Clean apartment plenty of parking"
United States
Rebecca P.
The price is £278
includes taxes & fees
18 Aug - 19 Aug
3 BR Apartment Near Wesleyan 201
Beach nearby

13. 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 £307
includes taxes & fees
7 Sept - 8 Sept
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Coffee/tea maker, fridge, microwave, oven

14. “3BR Home Near Wesleyan & Downtown Middletown

“3BR Home Near Wesleyan & Downtown Middletown
Washington Street Historic District
7.8 out of 10, Good, (6 reviews)
"Nice place"
United States
Jousette C.
The price is £234
includes taxes & fees
31 Aug - 1 Sept
“3BR Home Near Wesleyan & Downtown Middletown
Beach

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

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is £541
includes taxes & fees
9 Sept - 10 Sept
Beachside Bliss w/ Game Room, Gym & Golf Green
Interior

16. 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 £498
includes taxes & fees
8 Sept - 9 Sept
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Exterior

17. 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
9.8 out of 10, Exceptional, (17 reviews)
"Large, comfortable house in a tranquil part of town. "
United States
Daryl R.
The price is £636
includes taxes & fees
11 Sept - 12 Sept
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Dining

18. Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water

Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
Westbrook Center
9.4 out of 10, Exceptional, (3 reviews)
"We had a lovely time during our stay. The hosts were excellent with communication and quick responses throughout our stay. The 2 family suites were perfect for our families to all stay together during this trip. We would definitely book again! "
United States
Kate G.
Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
Interior

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
9.8 out of 10, Exceptional, (30 reviews)
"Wonderful house in a great location."
United States
Edward S.
The price is £770
includes taxes & fees
13 Aug - 14 Aug
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Exterior

20. Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (51 reviews)
"Great spot easy walk to the water and very close to town!"
United States
Genevieve G.
The price is £771
includes taxes & fees
18 Aug - 19 Aug
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlesex County Hotel Reviews

Grand Pequot Tower at Foxwoods

Grand Pequot Tower at Foxwoods

10/10 Excellent
"I enjoyed everything."
Mario 1-night trip
Posted 1 hour ago
Grand Pequot Tower at Foxwoods

Find out more about Middlesex County

Holiday Apartments in Middlesex County

Search for holiday rentals in Middlesex County on Expedia.co.uk! 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 rentals in Middlesex County
  • Use the map to find apartments and other holiday homes in the Middlesex County neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middlesex County while they last

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

Explore a world of travel with Expedia