Middlesex County Holiday Rentals

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Top Cities in Middlesex County

Top Holiday Rentals Destinations in Middlesex County

Our top choices for Middlesex County holiday rentals

Postcard Cabins Machimoodus

2.0 star property
9.6 out of 10, Exceptional, (52)
"Great stay"
The price is AU$273
includes taxes & fees
28 Aug - 29 Aug
Postcard Cabins Machimoodus

Shoreline Oasis

9.2 out of 10, Wonderful, (7)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is AU$409
includes taxes & fees
27 Aug - 28 Aug
Shoreline Oasis

COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

10.0 out of 10, Exceptional, (43)
"Amazing property, we loved everything about it, highly recommended, will stay again "
The price is AU$1,035
includes taxes & fees
27 Aug - 28 Aug
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

adorable ranch in beach community

10.0 out of 10, Exceptional, (45)
"Close to the shore and the heart of Old Saybrook. The house is very comfortable."
The price is AU$746
includes taxes & fees
22 Sept - 23 Sept
adorable ranch in beach community

Waterfront House with picture-perfect views from all 3 levels.

9.6 out of 10, Exceptional, (93)
"Our family had a fabulous week at the beach celebrating my 70th birthday. Lots of fun, food and laughter with the ocean as our background. This beach house had everything we needed as was as comfortable as our own home. "
Waterfront House with picture-perfect views from all 3 levels.

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (238)
"Had a great time. Will be back"
The price is AU$651
includes taxes & fees
11 Sept - 12 Sept
Cliffside Resort Condominiums

Charming houseboat in pleasant New London with AC, WiFi

9.6 out of 10, Exceptional, (10)
"Very nice people. Boat was roomy and well stocked but dirty. Toilet pump was broken and made loud noises all night. We were not informed this was an issue til checkout. Some other small issues "
The price is AU$504
includes taxes & fees
1 Sept - 2 Sept
Charming houseboat in pleasant New London with AC, WiFi

Safari Tent Glamping,S10-CedarPt, East Hampton, NY

The price is AU$444
includes taxes & fees
1 Sept - 2 Sept
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge

8.0 out of 10, Very good, (9)
Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (93)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
The price is AU$290
includes taxes & fees
27 Aug - 28 Aug
The Stern at Soundview · Beach+Ocean+Sunrise

Thames River Retreat · CT College+Casinos+USCGA

10.0 out of 10, Exceptional, (8)
"We found this home a perfect combination of being able to get away but also convenient to restaurants, stores, and activities. The view could not be beat and the house was clean and comfortable."
The price is AU$922
includes taxes & fees
28 Aug - 29 Aug
Thames River Retreat · CT College+Casinos+USCGA

Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

10.0 out of 10, Exceptional, (10)
"Such a fun, beautiful and unique stay. Would love to stay again!"
The price is AU$625
includes taxes & fees
10 Sept - 11 Sept
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

The Mast at Soundview · Beach+Ocean+Sunrise

2.0 star property
9.4 out of 10, Exceptional, (3)
"Nice place, little smaller than I was expecting, but location was close to the beach, info regarding access to the property was clear and easy to follow! Parking was assigned but other occupants decided not to utilize their assigned space and took ours. Be prepared to clean the studio before you leave to include dishes and take out the trash. Was surprised by the cleaning request. Overall great weekend!"
The price is AU$316
includes taxes & fees
3 Sept - 4 Sept
The Mast at Soundview · Beach+Ocean+Sunrise

Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath

10.0 out of 10, Exceptional, (5)
The price is AU$193
includes taxes & fees
1 Sept - 2 Sept
Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (139)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

The Crow's Nest at the Blue Anchor. Ready for 2025

2.0 star property
10.0 out of 10, Exceptional, (11)
"Nice to come home to a welcoming place with well-outfitted kitchen ready to cook breakfast!"
The Crow's Nest at the Blue Anchor. Ready for 2025

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

4.0 star property
9.6 out of 10, Exceptional, (135)
"Loved our stay and will be back"
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (93)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .

Safari Tent Glamping,S5-CedarPt, East Hampton, NY

9.0 out of 10, Wonderful, (2)
"We loved our tent, the view was great. The bed was super comfortable. We will definitely come back and hopefully stay longer. Also, the pizza is so good as was the watermelon Margherita."
The price is AU$454
includes taxes & fees
7 Sept - 8 Sept
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
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

Find out more about Middlesex County

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$193 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.