Middletown Holiday Rentals from AU$279: Search Short-Term Rentals

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Our top choices for Middletown holiday rentals

Coffee/tea maker, fridge, microwave, oven

1. 2BR Apartment Near Wesleyan 301

Washington Street Historic District

Joanne L.

includes taxes & fees

10 Sept - 11 Sept

2. #24 Serenity A Lakefront Cottage Retreat

Middletown

Rodrigo C.

includes taxes & fees

28 Sept - 29 Sept

3. 2BR Apartment Near Wesleyan 102

Washington Street Historic District

DANIEL M.

includes taxes & fees

10 Sept - 11 Sept

4. Family Stays: Middletown, CT

Middletown

Trisha T.

includes taxes & fees

30 Sept - 1 Oct

5. 3 BR Apartment Near Wesleyan 201

Washington Street Historic District

Rebecca P.

includes taxes & fees

10 Sept - 11 Sept

6. #29 - Modern 5 Bedroom/2 Bath

Middletown

Gail R.

includes taxes & fees

7 Oct - 8 Oct

7. Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Middletown

Lee S.

includes taxes & fees

23 Sept - 24 Sept

8. Private Apt in Middletown-Wesleyan 101

Washington Street Historic District

Kristoph

includes taxes & fees

10 Sept - 11 Sept

9. 3 BR Apartment Near Wesleyan 202

Washington Street Historic District

Douglas M.

includes taxes & fees

10 Sept - 11 Sept

10. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

East Haddam

Morainny

includes taxes & fees

14 Sept - 15 Sept

Smart TV, fireplace, books, music library

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

Haddam

Kate F.

includes taxes & fees

23 Sept - 24 Sept

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

Durham

Iris F.

includes taxes & fees

10 Sept - 11 Sept

13. Newly Remodeled with deck. Close to town center

Wallingford

Karen F.

includes taxes & fees

10 Sept - 11 Sept

14. All New 1BR with tons of Charm

Wallingford Center

Hannah Z.

includes taxes & fees

10 Sept - 11 Sept

15. Private Apartment in Berlin

Berlin

Shaun L.

includes taxes & fees

22 Sept - 23 Sept

16. The Cottage by the Woods -private getaway to relax

Meriden

includes taxes & fees

10 Sept - 11 Sept

17. All New Studio apartment in center of town

Wallingford Center

Nadine C.

includes taxes & fees

10 Sept - 11 Sept

1 bedroom, iron/ironing board, WiFi, bed sheets

18. Once the old Schools house now a newly furnished Apartment

Wallingford Center

Jeanette W.

includes taxes & fees

13 Sept - 14 Sept

19. Trumbull Apartments

Downtown Hartford

Nicolas

includes taxes & fees

12 Sept - 13 Sept

20. Newly Remodeled 1-BR Close to Everything yet Very Private

Wallingford

David M.

includes taxes & fees

20 Sept - 21 Sept

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Top Middletown Hotel Reviews

Clarion Inn North Haven - New Haven North

10/10 Excellent

"Tavern was nice with food . Under renovation so not as clean building supplies everywhere"

Hampton Inn & Suites Hartford/East Hartford

8/10 Good

"The property is undergoing renovation, so construction in the lobby was a bit challenging. But the staff under these circumstances was terrific! We had problems with the shower temperature in the room we were initially assigned, but when we left for the day, they held our bags, assigned us another room, and moved the bags there, and reduced the cost of our stay. Morning breakfast and attentive staff were a plus, and the East Hartford location had plenty of parking and allowed us to move around to surrounding communities. We would stay there again in a heartbeat."

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"Welcoming, helpful, friendly, professional front desk staff. My room was impeccably clean and tidy. The property is centrally-located with ease of accessibility to main roads and major highways, yet far enough off Boston Post Road to ensure a quiet, peaceful and restful stay. Overall, an outstanding, no-frills property! I look forward to staying here once again!"

Omni New Haven Hotel at Yale

8/10 Good

"Excellent staff and very clean facilities, including room, exercise room, and lobby. Backup plans for coffee/gift shop being open should be made as one day it was closed during prime morning hours. Only negative was it's right in the bar zone between Church and Chapel. If you are there Friday or Saturday, plan on being up quite late."

The Goodwin Hotel

8/10 Good

"Cleanliness was good, except not sure why but two nights in a row, they only made up one of the beds and left the other one completely undone. I had a two queen bed room, very spacious. I called the front desk to let them know, they apologized, but the next night the same thing happened and it was the other bed. I let the front desk know again, and I even asked if this is a Goodwin "troll" or something! A friend had this happen to her as well in the past when she stayed there. They assured me it is not, so it is very confusing."

Find out more about Middletown

Everything you need to know about Middletown 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 Middletown 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 Middletown holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Middletown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. 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 Middletown 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 Middletown holiday rentals we have selected for you start as low as AU$279 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown 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 Middletown 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 Middletown 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 Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there holiday rentals in Middletown?

Yes, there are holiday rentals in Middletown close to Kidcity Children's Museum, or you can select a more secluded option if you're looking for a relaxing stay. Middletown is known for its entertainment choices and festivals. Make sure you have time to check out the basketball games and university setting during your trip.

What are some of the best holiday rentals that Middletown has to offer?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This holiday home rental outside of Middletown is located on the beach, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Middletown?

With 10 Expedia holiday rentals, you're guaranteed to find just the right place for your Middletown stay.

What’s there to see and do in Middletown?

Family-friendly attractions include Kidcity Children's Museum and Van Vleck Observatory, whereas General Mansfield House and Connecticut River are a couple of great spots to enjoy the outdoors. Other places in town to visit include Wadsworth Mansion and Middletown Nature Gardens.

What’s a holiday rental in Middletown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middletown. Holiday rentals feature amenities like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips.

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Check prices for these dates

Our top choices for Middletown holiday rentals

1. 2BR Apartment Near Wesleyan 301

2. #24 Serenity A Lakefront Cottage Retreat

3. 2BR Apartment Near Wesleyan 102

4. Family Stays: Middletown, CT

5. 3 BR Apartment Near Wesleyan 201

6. #29 - Modern 5 Bedroom/2 Bath

7. Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

8. Private Apt in Middletown-Wesleyan 101

9. 3 BR Apartment Near Wesleyan 202

10. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

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

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

13. Newly Remodeled with deck. Close to town center

14. All New 1BR with tons of Charm

15. Private Apartment in Berlin

16. The Cottage by the Woods -private getaway to relax

17. All New Studio apartment in center of town

18. Once the old Schools house now a newly furnished Apartment

19. Trumbull Apartments

20. Newly Remodeled 1-BR Close to Everything yet Very Private

Find holiday rentals that suit your style

Top Middletown Hotel Reviews

Clarion Inn North Haven - New Haven North

Hampton Inn & Suites Hartford/East Hartford

New Haven Hotel

The Capitol Hotel

Pier Blue Inn Old Saybrook - Essex

Omni New Haven Hotel at Yale

Hotel Marcel New Haven, Tapestry Collection By Hilton

The Goodwin Hotel

Courtyard by Marriott Waterbury Downtown

Find out more about Middletown

Frequently asked questions

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