Holiday Rentals Middlesex County from £62: Find Short-Term Rentals & Holiday Accommodations

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Top cities in Middlesex County

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

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In two weeks

In two months

In three months

In four months

Our top choices for Middlesex County holiday 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

East Haddam

Kelvin

includes taxes & fees

10 Dec - 11 Dec

A modern kitchen with a central island, white cabinetry, stainless steel appliances, and a wooden floor.

2. 2BR Apartment Near Wesleyan 301

Washington Street Historic District

Joanne L.

A large, white, multi-story building with a prominent tower and a flag on top.

3. Walk To Goodspeed Opera House!

East Haddam

Anonymous traveller

includes taxes & fees

17 Nov - 18 Nov

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

Washington Street Historic District

DANIEL M.

includes taxes & fees

12 Nov - 13 Nov

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

Haddam

Kristy C.

includes taxes & fees

17 Nov - 18 Nov

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

Washington Street Historic District

Rebecca P.

A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

7. 1-bedroom cottage with Grove Beach 🏖️ access.

Clinton

Marcy C.

includes taxes & fees

12 Nov - 13 Nov

8. Family Stays: Middletown, CT

Middletown

Audrey F.

includes taxes & fees

16 Nov - 17 Nov

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.

Durham

Iris F.

includes taxes & fees

15 Nov - 16 Nov

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

Clinton

Wink V.

includes taxes & fees

13 Nov - 14 Nov

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

Main Street Historic District

includes taxes & fees

12 Nov - 13 Nov

A beach with waves, a clear sky, and a sandy shore.

12. Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Westbrook Center

Mason T.

includes taxes & fees

12 Nov - 13 Nov

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

Westbrook

Morgan M.

includes taxes & fees

1 Dec - 2 Dec

An outdoor kitchen area with a stone fireplace, grill, and built-in refrigerator.

14. Cozy 1 bedroom private farmhouse apartment

Durham

includes taxes & fees

30 Nov - 1 Dec

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

Saybrook Manor

Alexis L.

includes taxes & fees

16 Nov - 17 Nov

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!

Clinton

Juliana A.

includes taxes & fees

12 Nov - 13 Nov

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.

Old Saybrook

Karol T.

includes taxes & fees

15 Nov - 16 Nov

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

Westbrook Center

Francine F.

includes taxes & fees

12 Nov - 13 Nov

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 Center

includes taxes & fees

1 Dec - 2 Dec

A compact kitchen with white cabinets, a built-in oven, and a dining table with chairs.

20. Private Apt in Middletown-Wesleyan 101

Washington Street Historic District

Kristoph

includes taxes & fees

12 Nov - 13 Nov

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Top Middlesex County Hotel Reviews

A living room with a stone fireplace, grey sofas, and a coffee table.

The Captain Stannard

Westbrook Center

10/10 Excellent

Jessica

A round outdoor fire pit with flames, surrounded by wicker furniture and a white cushion.

Westbrook Inn B&B

Westbrook Center

8/10 Good

Nicola

An outdoor patio with a fire feature, seating, and a building with large windows and a stone facade.

Home2 Suites by Hilton East Haven New Haven

The Centre

10/10 Excellent

Chris

A modern building entrance with a covered walkway, a white car parked in front, and two people near the entrance.

Hotel Marcel New Haven, Tapestry Collection By Hilton

Long Wharf

10/10 Excellent

Iain

A restaurant with wooden beams, large windows, and blue chairs. Tables are set with wine glasses and cutlery.

The Whaler's Inn

Mystic

10/10 Excellent

This hotel has one of the best, if not the best, sites in Mystic. Our room had a great view of the river and swing bridge. Whilst there's no elevator and we were on the top floor help with our baggage on arrival and departure were readily and quickly available. Room was clean and comfortable and the bed provided a great night's sleep. Only slight let down was the included "continental" breakfast. But if you want a more varied or larger meal there are plenty of places nearby. Recommended.

David

A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

The Shoals Suites and Slips

Southold

10/10 Excellent

Paul

An outdoor patio area with a fire pit, seating, and umbrellas.

Hampton Inn & Suites Rocky Hill - Hartford South

Rocky Hill

10/10 Excellent

Loved our stay. Arrived exhausted after a long flight from London, followed by a drive from JFK. Greeted warmly, offered welcome packs of water. There was system problems and they couldn’t get our room key set so offered to let us into our room with the master key, and slide room keys under the door once they fixed the system. Which they did. We had the best sleep. Comfiest hotel bed hands down. Breakfast was excellent, literally no complaints about anything it was all delicious, fresh. Every...

Rachel

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, apart-hotels, 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 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 £62 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.

Search Holiday Rentals in Middlesex County

Change your mind

Treat yourself

Be picky

Top cities in Middlesex County

Old Saybrook

Check prices for these dates

Our top choices for Middlesex County holiday rentals

1. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2. 2BR Apartment Near Wesleyan 301

3. Walk To Goodspeed Opera House!

4. 2BR Apartment Near Wesleyan 102

5. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

6. 3 BR Apartment Near Wesleyan 201

7. 1-bedroom cottage with Grove Beach 🏖️ access.

8. Family Stays: Middletown, CT

9. New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

10. The gardners Cottage 1 mile from long Island Sound - pet friendly

11. Conference Room Rental no sleeping arrangements

12. Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

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

14. Cozy 1 bedroom private farmhouse apartment

15. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

16. Charming beach home, complete with pool & cozy guest house!

17. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

18. Adorable Cottage with Cottage porch, walk to water & town

19. Westbrook Getaway-Near Beaches, Train & Shoreline

20. Private Apt in Middletown-Wesleyan 101

Find holiday rentals that suit your style

Top Middlesex County Hotel Reviews

The Captain Stannard

10/10 Excellent

Find out more about Middlesex County

Middlesex County holiday rentals: An excellent choice for every season

How to find incredible deals on Middlesex County rentals

Explore a world of travel with Expedia