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

Vacation Rentals in Middlesex County

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Top Cities in Middlesex County

A coastal town with a lighthouse, houses, and a river.
Vacation RentalsVacation Rentals

Old Saybrook

Old Saybrook

Our top choices for Middlesex County vacation 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, (222 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
$175 nightly
The price is $201
Dec 13 - Dec 14
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A modern kitchen with a central island, wooden flooring, and a ceiling light fixture.

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
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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 traveler
$177 nightly
The price is $202
Dec 10 - Dec 11
Total with taxes and fees
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.
$223 nightly
The price is $254
Nov 14 - Nov 15
Total with taxes and fees
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.
$223 nightly
The price is $254
Dec 1 - Dec 2
Total with taxes and fees
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, (67 reviews)
"Cozy vrbo with a great location to the beach, outlets shops and excellent restaurants!"
United States
Marcy C.
$222 nightly
The price is $253
Nov 19 - Nov 20
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Veterans Park, near the house

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.
$221 nightly
The price is $252
Nov 16 - Nov 17
Total with taxes and fees
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.
$1,004 nightly
The price is $1,143
Nov 13 - Nov 14
Total with taxes and fees
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)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
$300 nightly
The price is $341
Nov 13 - Nov 14
Total with taxes and fees
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
$775 nightly
The price is $883
Nov 13 - Nov 14
Total with taxes and fees
Conference Room Rental no sleeping arrangements
A modern kitchen with a built-in oven, a refrigerator, and a window with a view of trees.

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.
$271 nightly
The price is $308
Nov 16 - Nov 17
Total with taxes and fees
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

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.
$525 nightly
The price is $598
Nov 17 - Nov 18
Total with taxes and fees
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
$250 nightly
The price is $284
Nov 29 - Nov 30
Total with taxes and fees
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.
$481 nightly
The price is $548
Nov 16 - Nov 17
Total with taxes and fees
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.
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.
$399 nightly
The price is $455
Nov 15 - Nov 16
Total with taxes and fees
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.
$478 nightly
The price is $547
Nov 13 - Nov 14
Total with taxes and fees
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
$351 nightly
The price is $401
Dec 2 - Dec 3
Total with taxes and fees
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
$231 nightly
The price is $264
Nov 16 - Nov 17
Total with taxes and fees
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

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent
"Friendly staff, rooms were clean."
Jennifer 1-night trip
Posted 9 hours ago
Best Western Executive Hotel Of New Haven - West Haven

Find out more about Middlesex County

Discover your perfect Middlesex County vacation rental with Expedia

How many vacation rentals are available in Middlesex County?


Expedia has plenty of vacation rentals to choose from in and around  Middlesex County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Middlesex County?


The selection of Middlesex County vacation rentals we have selected for you start as low as $201 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Middlesex County?


Vacation rentals in Middlesex County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Middlesex County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Middlesex County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Middlesex County vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Middlesex County?


Find vacation rentals in Middlesex County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Middlesex County.  


What amenities are available in a vacation rental in Middlesex County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Middlesex County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Middlesex County?   


Everytime is a great time to head to Middlesex County! Staying in a Middlesex County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Middlesex County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Middlesex County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Middlesex County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Middlesex County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.