Middletown Holiday Rentals, Connecticut: Private House Rentals

A forested landscape with a winding dirt road and power lines.

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Go beyond your typical stay in Middletown

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Our top choices for Middletown hotels

1. Inn at Middletown

Washington Street Historic District

Dale

4.385.976 ₫

5.566.012 ₫ total

includes taxes & fees

21 Sept - 22 Sept

2. Springhill Suites by Marriott Hartford Cromwell

Cromwell

Nancy K

3.106.733 ₫

3.572.743 ₫ total

includes taxes & fees

26 Aug - 27 Aug

3. Hampton Inn & Suites Rocky Hill - Hartford South

Rocky Hill

Fabiola

3.198.550 ₫

3.678.332 ₫ total

includes taxes & fees

31 Aug - 1 Sept

Suite, 1 King Bed, Non Smoking, Jetted Tub

4. Best Western Plus New England Inn & Suites

Berlin

Veronica

2.733.925 ₫

3.144.014 ₫ total

includes taxes & fees

26 Aug - 27 Aug

Suite, 1 King Bed with Sofa bed, Non Smoking

5. Comfort Inn & Suites Meriden East

Meriden

Sharmarie

2.363.178 ₫

2.717.655 ₫ total

includes taxes & fees

15 Sept - 16 Sept

6. Sheraton Hartford South Hotel

Rocky Hill

Brian

3.185.054 ₫

3.662.812 ₫ total

includes taxes & fees

13 Sept - 14 Sept

7. Holiday Inn Express Hartford South - Rocky Hill by IHG

Rocky Hill

Axandre

2.793.449 ₫

3.212.467 ₫ total

includes taxes & fees

20 Sept - 21 Sept

8. Fairfield by Marriott Inn & Suites Wallingford New Haven

Wallingford

Thierry

3.265.986 ₫

3.755.884 ₫ total

includes taxes & fees

20 Sept - 21 Sept

9. Homewood Suites by Hilton Wallingford-Meriden

Wallingford

Timothy

3.750.271 ₫

4.312.812 ₫ total

includes taxes & fees

7 Sept - 8 Sept

10. Days Inn by Wyndham Southington

Southington

LAWRENCE

2.323.523 ₫

2.672.051 ₫ total

includes taxes & fees

26 Aug - 27 Aug

11. Red Roof Inn Meriden

Meriden

David

2.093.516 ₫

2.407.543 ₫ total

includes taxes & fees

16 Sept - 17 Sept

12. Extended Stay America Suites Hartford Meriden

Meriden

Casey

2.584.332 ₫

2.972.021 ₫ total

includes taxes & fees

26 Aug - 27 Aug

13. Courtyard New Haven Wallingford

Wallingford

Marjory

3.628.873 ₫

4.173.204 ₫ total

includes taxes & fees

27 Aug - 28 Aug

14. Hilton Garden Inn Wallingford/Meriden

Wallingford

Daylene

3.627.886 ₫

4.172.069 ₫ total

includes taxes & fees

6 Sept - 7 Sept

15. Courtyard by Marriott Hartford Cromwell

Cromwell

Iurii

3.981.826 ₫

4.579.100 ₫ total

includes taxes & fees

7 Sept - 8 Sept

16. Hampton Inn & Suites Hartford/East Hartford

East Hartford

Ellen

2.769.215 ₫

3.184.598 ₫ total

includes taxes & fees

30 Aug - 31 Aug

17. Holiday Inn Express & Suites Meriden by IHG

Meriden

George

2.793.449 ₫

3.212.467 ₫ total

includes taxes & fees

20 Sept - 21 Sept

18. Solano Inn

Portland

Douglas

2.131.102 ₫

2.450.767 ₫ total

includes taxes & fees

26 Aug - 27 Aug

19. Howard Johnson by Wyndham Hartford South – Rocky Hill

Rocky Hill

Rhett

2.336.476 ₫

2.686.947 ₫ total

includes taxes & fees

23 Aug - 24 Aug

20. Days Inn by Wyndham Berlin Meriden

Berlin

LaResse

1.809.215 ₫

2.080.597 ₫ total

includes taxes & fees

21 Sept - 22 Sept

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Where to stay in Middletown

Find the best Middletown areas for the activities you enjoy most.Learn more about Middletown

Washington Street Historic District

Washington Street Historic District

You'll enjoy the museums and live music in Washington Street Historic District. You might want to make time for a stop at General Mansfield House or Kidcity Children's Museum.

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Stay near popular Middletown attractions

A large white building with columns and a central staircase.

Wadsworth Mansion

This Beaux-Arts masterpiece invites you into the grandeur of early 20th century American aristocracy. Wander through elegant interiors on Wednesday tours, then explore picturesque trails and gardens.

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A waterfront promenade with a curved walkway, street lamps, and a backdrop of autumn-colored trees.

Harbor Park

8.0/10 (5 reviews)

Harbour Park offers tranquil riverside paths along the Connecticut River with perfect sunset views. Enjoy a picnic while watching boats pass by, or time your visit for the annual rowing races and Fourth of July fireworks.

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Wesleyan University

8.6/10 (189 reviews)

Wesleyan University's historic 316-acre campus blends 19th-century architecture with cutting-edge facilities. Experience the vibrant intellectual community that has defined this liberal arts institution since 1831.

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General Mansfield House

This stately Federal-style mansion showcases Middletown's Civil War heritage through period rooms and rare artefacts. Explore historical exhibits, then stroll gardens featuring a magnificent 150-year-old ginkgo tree.

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Middletown Nature Gardens

Wander through 18 acres of diverse Connecticut ecosystems, from woodlands to a rare red maple swamp. The 200-year-old "Bee Tree" sugar maple stands as a living monument to the garden's natural heritage.

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Dooley Pond Public Access

Dooley Pond offers a serene freshwater fishing haven where anglers pursue largemouth bass and yellow perch. Launch your small boat from this peaceful access point and enjoy Connecticut's natural tranquility.

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Ron McCutcheon Park

This lakeside sanctuary honours Ron McCutcheon, who taught generations of local children to swim. Enjoy the sandy beach, picnic under pavilions, or explore walking trails through the 25-acre wildlife preserve.

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Kidcity Children's Museum

10.0/10 (1 review)

This artist-crafted museum features three floors of imaginative play spaces designed for children ages 1-7. Explore medieval villages, fishing ships, and space-age adventures in detailed settings that spark creativity.

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Learn more about Middletown

Wesleyan University's stunning campus and the Connecticut River waterfront offer perfect spots for afternoon strolls and picnics. Explore Main Street's indie bookshops and farm-to-table restaurants, then catch a show at the historic Oddfellows Playhouse where locals gather.

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A waterfall cascading over rocks into a calm pool surrounded by forest.

Top Middletown Hotel Reviews

Hotel Marcel New Haven, Tapestry Collection By Hilton

10/10 Excellent

"Very nice and clean room. Windows are sound proof."

The Capitol Hotel

10/10 Excellent

"Beautiful view of the Capitol building!"

Red Roof Inn Meriden

10/10 Excellent

"LOVED IT"

New Haven Hotel

10/10 Excellent

"It was a nice experience the staff was very helpful"

Holiday Inn Express Southington by IHG

10/10 Excellent

"Clean room. Breakfast was good especially the biscuits"

Pier Blue Inn Old Saybrook - Essex

8/10 Good

"Clean and comfortable room. Very dated furniture."

Water's Edge Resort & Spa

8/10 Good

"I booked through Expedia because I believed the price I was quoted would be the final cost other than incidentals. Additional resort fees and tax were added to the final bill. Over 130.00 in unexpected cost. Be aware when booking."

Motel 6 New Haven - Branford, CT

10/10 Excellent

"Clean room when you need.Staff when you need are there.Shops nearby but better rent a car.Laundry ok."

Home2 Suites by Hilton East Haven New Haven

10/10 Excellent

"Excellent - it’s a shame one can not purchase alcohol"

More cheap stays in Middletown

Motel 6 Wethersfield, CT - Hartford

1341 Silas Deane Hwy Wethersfield CT

1.629.381 ₫

1.873.893 ₫ total

8 Sept - 9 Sept

includes taxes & fees