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 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 NZ$341
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.
The price is NZ$472
includes taxes & fees
11 Nov - 12 Nov
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 NZ$383
includes taxes & fees
10 Dec - 11 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 NZ$411
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 NZ$442
includes taxes & fees
7 Dec - 8 Dec
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.
The price is NZ$540
includes taxes & fees
11 Nov - 12 Nov
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.
The price is NZ$420
includes taxes & fees
11 Nov - 12 Nov
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 NZ$452
includes taxes & fees
16 Nov - 17 Nov
Family Stays: Middletown, CT
A modern kitchen with a central island, bar stools, and pendant lighting.

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 NZ$1,991
includes taxes & fees
12 Nov - 13 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 NZ$604
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 NZ$1,582
includes taxes & fees
11 Nov - 12 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 NZ$539
includes taxes & fees
11 Nov - 12 Nov
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 NZ$1,083
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 NZ$478
includes taxes & fees
30 Nov - 1 Dec
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 NZ$987
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 NZ$2,396
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 NZ$794
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.
The price is NZ$976
includes taxes & fees
11 Nov - 12 Nov
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 NZ$726
includes taxes & fees
1 Dec - 2 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 NZ$461
includes taxes & fees
12 Nov - 13 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

New Haven Hotel

New Haven Hotel

10/10 Excellent
"This is my go-to hotel when I travel to CT. Excellent rooms, great interior design, and a lobby that's also very amenable to working travelers. And the staff is amazing! I've never had a bad experience. Definitely recommend"
Taylor-Ivory 3-night trip
Posted 1 hour ago
New Haven Hotel

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 favorite 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 depends 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 selected for you start as low as NZ$341 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.