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

Middlesex County Holiday Rentals

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Our top choices for Middlesex County holiday rentals

A cabin with a large window, surrounded by trees.

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, (182 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 AU$345
includes taxes & fees
23 Sept - 24 Sept
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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.

2. 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, (36 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 AU$358
includes taxes & fees
31 Aug - 1 Sept
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
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, (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 AU$342
includes taxes & fees
22 Sept - 23 Sept
Walk To Goodspeed Opera House!
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

4. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (53 reviews)
"We enjoyed our stay"
United States
JM B.
The price is AU$310
includes taxes & fees
15 Sept - 16 Sept
1-bedroom cottage with Grove Beach 🏖️ access.
A modern kitchen with a central island, white cabinetry, stainless steel appliances, and a wooden floor.

5. 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 AU$509
includes taxes & fees
30 Aug - 31 Aug
2BR Apartment Near Wesleyan 301
A lakeside property with a gazebo, dock, kayaks, and a flag.

6. 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 AU$418
includes taxes & fees
7 Sept - 8 Sept
Lakeview Carriage House with Spectacular Sunset Views
A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

7. 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 AU$447
includes taxes & fees
1 Sept - 2 Sept
The gardners Cottage 1 mile from long Island Sound - pet friendly
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

8. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
8.8 out of 10, Excellent, (5 reviews)
The price is AU$444
includes taxes & fees
26 Aug - 27 Aug
2BR Apartment Near Wesleyan 102
A modern kitchen with dark cabinetry, a marble countertop, and a dining area with a table and chairs.

9. 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 AU$542
includes taxes & fees
15 Sept - 16 Sept
3 BR Apartment Near Wesleyan 201
A beach with waves, a clear sky, and a sandy shore.

10. 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 AU$507
includes taxes & fees
22 Sept - 23 Sept
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
A modern kitchen with white cabinets, a stainless steel refrigerator, a dining area with two chairs, and a coffee machine.

11. “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 AU$402
includes taxes & fees
31 Aug - 1 Sept
“3BR Home Near Wesleyan & Downtown Middletown
A stone fire pit with two Adirondack chairs, a wooden fence, and a black building with a red door.

12. NEW Coastal Cottage 2 Miles to Beach + Lake Access

NEW Coastal Cottage 2 Miles to Beach + Lake Access
Clinton
10.0 out of 10, Exceptional, (8 reviews)
"We really enjoyed our stay here. The house has a cozy, homey feel and was a nice place to come back to after being out for the day. It was quiet, comfortable, and had a relaxed vibe that made the trip easy.The location was a big plus for us. Hammonasset Beach was only a few minutes away, and Madison center was just as close, which made it easy to grab dinner or pop out for anything we needed. The outdoor fireplace was also a really nice touch and made the evenings feel special.Overall, it was a...
United States
Moe B.
The price is AU$524
includes taxes & fees
26 Aug - 27 Aug
NEW Coastal Cottage 2 Miles to Beach + Lake Access
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

13. 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 AU$823
includes taxes & fees
21 Sept - 22 Sept
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

14. 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 AU$974
includes taxes & fees
22 Sept - 23 Sept
Beachside Bliss w/ Game Room, Gym & Golf Green
A glass-enclosed patio with a wooden table and wicker chairs, surrounded by glass doors and windows offering views of a wooded area.

15. LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!

LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
Clinton
9.8 out of 10, Exceptional, (6 reviews)
"Was very happy with how wonderfully beautiful the place was. The host was excellent and answered any questions I had promptly. I really appreciate how nice he was."
United States
Elizabeth C.
The price is AU$1,077
includes taxes & fees
9 Sept - 10 Sept
LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
A two-story house with a front porch, a garage, and a well-maintained lawn.

16. 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 AU$1,188
includes taxes & fees
7 Sept - 8 Sept
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
A dining area with a wooden table, white chairs, a checkered tablecloth, a vase with flowers, and a decorative ceiling light.

17. 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.
The price is AU$1,199
includes taxes & fees
26 Aug - 27 Aug
Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
An aerial view of a marina with boats docked, surrounded by residential buildings and greenery.

18. 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 AU$915
includes taxes & fees
24 Sept - 25 Sept
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
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
9.8 out of 10, Exceptional, (30 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 AU$1,387
includes taxes & fees
26 Aug - 27 Aug
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 AU$1,270
includes taxes & fees
26 Aug - 27 Aug
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

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent
"Awesome place to stay with the complimentary breakfast"
Teresa 6-night trip
Posted 2 hours ago
Best Western Executive Hotel Of New Haven - West Haven

Find out more about Middlesex County

Everything you need to know about Middlesex County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlesex County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlesex County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Middlesex County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlesex County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlesex County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Middlesex County holiday rentals we have chosen for you start as low as AU$310 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Middlesex County rentals

At Expedia, we put the best Middlesex County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middlesex County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlesex County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlesex County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.