Middlebury Holiday Rentals, Connecticut: Private House Rentals

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Our top choices for Middlebury hotels

A spacious hotel lobby with wooden beams, a central seating area, and large windows offering a view.

A courtyard with stone pathways, various shrubs, and a small tree.

A spacious lobby with a stone fireplace, leather sofas, and a wooden ceiling.

A spacious hall with round tables and chairs, wooden beams on the ceiling, and large windows allowing natural light.

1. Heritage Hotel, Golf & Conference Center

Southbury

Zuleika

3.136.753 ₫

4.057.112 ₫ total

includes taxes & fees

8 Sept - 9 Sept

A hotel lobby with a modern design, featuring a seating area with sofas, a fireplace, and a television mounted on the wall.

A bar area with stools, shelves of beverages, and a coffee machine.

A hotel room with a large bed, a desk with a computer, a chair, and a small table.

2. Courtyard by Marriott Waterbury Downtown

Waterbury

Neliniewattie

2.320.942 ₫

2.669.083 ₫ total

includes taxes & fees

31 Aug - 1 Sept

A modern lobby with a stone wall, seating area, and a bar with bottles.

A conference room with round tables, chairs, and a buffet area.

A hotel room with a bed, bedside lamps, a TV, and a desk with drawers.

A spacious room with a wooden floor, large windows, and a chandelier.

3. Wyndham Southbury

Southbury

Andrea

2.416.127 ₫

2.778.546 ₫ total

includes taxes & fees

20 Sept - 21 Sept

A Hampton Inn hotel with a modern design, featuring a well-lit entrance and multiple floors.

A hotel lobby with a dining area, a kitchen, and a seating area with a TV and artwork.

A gym with treadmills, dumbbells, and exercise balls.

A hotel room with a large bed, a desk with a television, a chair, and a desk lamp.

4. Hampton Inn Waterbury

Waterbury

Christina

3.081.116 ₫

3.543.283 ₫ total

includes taxes & fees

7 Sept - 8 Sept

An outdoor patio with a fire pit, wicker furniture, and a pergola structure.

A modern lobby with a fireplace, comfortable seating, and framed pictures on the walls.

A hotel with multiple floors, a central entrance, and a well-maintained lawn.

A modern lobby with a large sofa, armchairs, a coffee table, and a reception desk.

5. Homewood Suites by Hilton Southington, CT

Southington

Stephenie

3.613.889 ₫

4.155.973 ₫ total

includes taxes & fees

6 Sept - 7 Sept

A modern building with a large digital welcome sign, a convention center sign, and a parking garage entrance.

A coffee station with two coffee machines, a coffee press, and various coffee pods and cups.

A Holiday Inn Express hotel with a covered entrance, a parking lot, and a clear sky.

A poolside wheelchair by a pool with lounge chairs and a potted plant in the background.

6. Holiday Inn Express Southington by IHG

Southington

Rodwell

2.482.626 ₫

2.855.020 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A hotel room with a bed, white pillows, a bedside table with a phone, and a wall-mounted TV displaying a scenic sunset.

A kitchen area with a counter, a microwave, a coffee machine, and a display case with pastries.

A Days Inn sign with a sunburst design, surrounded by trees.

A bathroom with a bathtub, toilet, and granite countertop sink.

7. Days Inn by Wyndham Torrington

Torrington

Juan

2.527.219 ₫

2.906.302 ₫ total

includes taxes & fees

1 Sept - 2 Sept

An outdoor patio area with a stone fire pit, wicker furniture, and a bar area with a flat-screen TV.

A swimming pool with lounge chairs and tables, large windows, and a view of the outside.

A modern kitchen with dark cabinetry, stainless steel appliances, a dining table with chairs, and pendant lighting.

A spacious lobby with multiple seating areas, a large flat-screen TV, and a fireplace.

8. Residence Inn by Marriott New Haven Hamden

Hamden

Constance

4.407.182 ₫

5.068.259 ₫ total

includes taxes & fees

6 Sept - 7 Sept

A landscaped garden with a large rock, yellow flowers, and a weeping willow tree.

A building with a sign indicating it is an AAA Approved office. There are trees and shrubs in front of the building.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, a sink, and a television mounted on the wall.

A hotel room with two beds, a desk with a TV, a microwave, and a coffee maker.

9. Cheshire Welcome Inn

Cheshire

Carol

2.323.550 ₫

2.672.083 ₫ total

includes taxes & fees

31 Aug - 1 Sept

An outdoor seating area with wicker furniture, a stone fireplace, and lanterns.

A spacious room with a large wooden dining table, comfortable seating, and a bookshelf filled with books.

An indoor swimming pool with red lounge chairs and a brick wall.

A bar area with red chairs, a television mounted on the wall, and shelves with bottles.

10. Trumbull Marriott Shelton

Trumbull

Andrew

3.885.622 ₫

4.468.465 ₫ total

includes taxes & fees

31 Aug - 1 Sept

A hotel room with a bed, bedside table, desk, chair, and a mirror.

An indoor swimming pool with clear blue water, surrounded by lounge chairs and a bench.

A hotel with a covered parking area, multiple columns, and a building with a flat roof.

A multi-story hotel with a parking lot and a road in the foreground.

11. Danbury Inn & Suites

Danbury

Philip

3.129.360 ₫

3.598.764 ₫ total

includes taxes & fees

1 Sept - 2 Sept

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

A spacious living area with a fireplace, a reception desk, and a large window.

A modern room with white leather sofas, a small round table, a stone fireplace, and large windows.

A spacious dining area with high tables and chairs, a patterned carpet, and pendant lighting.

12. Fairfield by Marriott Inn & Suites Wallingford New Haven

Wallingford

Thierry

3.262.358 ₫

3.751.712 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A modern lobby with seating, a dining area, and large windows.

A modern kitchen with a central island, bar seating, and a high ceiling with exposed beams.

A modern kitchen area with a central island, a coffee machine, and a sign that reads 'KITCHEN'.

A modern living room with a sofa, ottoman, and a TV mounted on the wall.

13. Clarion Inn North Haven - New Haven North

North Haven

Katie

2.792.954 ₫

3.211.897 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A modern kitchen with wooden cabinets, a white countertop, and various food items displayed.

A hotel room with a large bed, a desk, a chair, and a window.

A snack display in a hotel lobby with various brands of chips and snacks.

A gym with exercise equipment, a bench, a medicine ball, and a rack of dumbbells.

14. Hampton Inn & Suites New Haven - South - West Haven

West Haven

Linda

2.626.042 ₫

3.019.948 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A Holiday Inn hotel with a covered entrance and green lighting.

A modern restaurant interior with a curved counter, seating area, and a wooden ceiling.

A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.

An indoor swimming pool with a lifeguard warning sign, chairs, and a view of the outside.

15. Holiday Inn Cheshire - Southington by IHG

Southington

Carlos

2.972.892 ₫

3.418.826 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A modern lobby with a fireplace, seating area, and a reception desk.

A multi-story hotel with a stone facade and a covered entrance.

A modern bar area with high stools and a central round table, surrounded by bar chairs.

A hotel lobby with a pool table, seating area, bar, and fireplace.

16. Hyatt House Shelton

Shelton

Shenise

3.755.232 ₫

4.318.516 ₫ total

includes taxes & fees

6 Sept - 7 Sept

A modern interior with wooden panel walls, a reception desk, and a seating area with chairs.

An outdoor patio area with wooden benches, planters with greenery, and a pergola with string lights.

A hotel room with two beds, a desk, a chair, a TV, and a large forest-themed painting on the wall.

A modern restaurant with wooden panel walls, a flat-screen TV, and a variety of seating including tables and booths.

17. Days Inn by Wyndham Southington

Southington

LAWRENCE

2.320.942 ₫

2.669.083 ₫ total

includes taxes & fees

31 Aug - 1 Sept

A breakfast buffet with various food items, including pastries, bread, and fruits.

A reception area with a stone counter, framed certificates on the wall, and a sign indicating the manager is on duty.

A hotel room with a bathroom, a TV, a chair, and a desk.

A lobby with a sofa, a reception desk, and a view of the outside.

18. Quality Inn Waterbury East

Waterbury

Wilfred

2.416.127 ₫

2.778.546 ₫ total

includes taxes & fees

6 Sept - 7 Sept

A bar area with a curved counter, bar stools, and a television screen above the bar.

A lobby with a reception desk, seating area with sofas and chairs, and a decorative wall with a light fixture.

A hotel room with a sofa, a bed, a TV, and a desk with a telephone.

A bar area with a curved counter, a refrigerated display case, and several wooden bar stools.

19. Hyatt Place Milford / New Haven

Milford

Coran

3.302.779 ₫

3.798.195 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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

An indoor swimming pool with clear water, tiled walls, and a 'No Diving' sign.

A hotel room with a dining table, chairs, a sofa, a TV, a fireplace, and a door.

A hotel room with a sofa, a desk with a computer, a TV, a dining table with chairs, and a lamp.

20. Residence Inn by Marriott Southington

Southington

Anne

3.729.154 ₫

4.288.527 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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Where to stay in Middlebury

Find the best Middlebury areas for the activities you enjoy most.

Middlebury Center Historic District

Middlebury Center Historic District

Visitors to Middlebury Center Historic District enjoy its historical sites, and if you want to do some exploring, Lake Quassapaug is worth a stop.

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Stay near popular Middlebury attractions

Quassy Amusement Park

8.2/10 (21 reviews)

This century-old Connecticut park balances nostalgia with modern thrills, featuring the award-winning Wooden Warrior coaster and lakeside beach. Rent a waterpark cabana for a premium experience during hot summer days.

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Learn more about Middlebury

Quassy Amusement Park offers thrilling rides and a refreshing lakeside beach where families cool off during summer months. History buffs can explore the 1800s buildings at Middlebury Historical Society Museum, while hikers enjoy scenic trails through Hop Brook Lake Park.

See all hotels in Middlebury

A weathered stone structure with steps and a small opening, surrounded by fallen leaves and moss.

Top Middlebury Hotel Reviews

New Haven Hotel

8/10 Good

"Very spacious room. Tired and a bit musty but clean and well-maintained. Lots of room to spread out; bathroom more than adequate. I really appreciated the enclosed, secure garage so close with the use of the footbridge. I do wish I'd been told I needed my room key to get out of the garage - I'd already turned it in. If it wasn't for the parking attendant letting me out, I'd have been stuck running across the street to get my key back from the front desk, all while blocking the exit."

Hampton Inn & Suites New Haven - South - West Haven

10/10 Excellent

"Everything was clean, staff were friendly, all good."

Holiday Inn Express Southington by IHG

10/10 Excellent

"Thank you"

Comfort Inn & Suites Danbury-Bethel

8/10 Good

"Very convenient location but our room location was much quieter on our first stay. Perhaps the hotel was more fully booked, but our first room was much more private."

Wyndham Southbury

10/10 Excellent

"Adequate stay, bar staff lovely and friendly Odd odor in corner of hallway needs to freshen up Popular place for many travelers."

La Quinta Inn & Suites by Wyndham New Haven

8/10 Good

"All fine. Room was cooled to 63F which was welcome but a bit too chilly for sleep; easily controlled. All else fine, room clean and queen bed was supportive, pillows comfortable."

More cheap stays in Middlebury

Red Roof Inn Meriden

10 Bee St Meriden CT

2.229.408 ₫

2.563.728 ₫ total

1 Sept - 2 Sept

includes taxes & fees

Holiday Inn Express Southington by IHG

120 Laning St Southington CT

2.482.626 ₫

2.855.020 ₫ total

7 Sept - 8 Sept

includes taxes & fees

8.6/10 Excellent! (1,427 reviews)

Microtel Inn & Suites by Wyndham Bethel/Danbury

80 Benedict Rd Bethel CT

2.712.112 ₫

3.118.929 ₫ total

29 Sept - 30 Sept

includes taxes & fees

8.2/10 Very good! (1,002 reviews)

Extended Stay America Suites Shelton Fairfield County

945 Bridgeport Ave Shelton CT

2.816.163 ₫

3.238.627 ₫ total

31 Aug - 1 Sept

includes taxes & fees

7.4/10 Good! (1,005 reviews)

Best Western Executive Hotel Of New Haven - West Haven

490 Saw Mill Rd West Haven CT

2.960.375 ₫

3.404.431 ₫ total

16 Sept - 17 Sept

includes taxes & fees

8.2/10 Very good! (1,823 reviews)

Comfort Inn & Suites Danbury-Bethel

80 Newtown Road Danbury CT

3.108.498 ₫

3.574.773 ₫ total

20 Sept - 21 Sept

includes taxes & fees

8.4/10 Very good! (842 reviews)

Hotels in Middlebury with star rating

Frequently asked questions

What's the seasonal weather in Middlebury?

The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. Average annual precipitation for Middlebury is 1410 mm.

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Find hotels in Middlebury, CT from 1.769.392 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Middlebury

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Middlebury hotels

1. Heritage Hotel, Golf & Conference Center

2. Courtyard by Marriott Waterbury Downtown

3. Wyndham Southbury

4. Hampton Inn Waterbury

5. Homewood Suites by Hilton Southington, CT

6. Holiday Inn Express Southington by IHG

7. Days Inn by Wyndham Torrington

8. Residence Inn by Marriott New Haven Hamden

9. Cheshire Welcome Inn

10. Trumbull Marriott Shelton

11. Danbury Inn & Suites

12. Fairfield by Marriott Inn & Suites Wallingford New Haven

13. Clarion Inn North Haven - New Haven North

14. Hampton Inn & Suites New Haven - South - West Haven

15. Holiday Inn Cheshire - Southington by IHG

16. Hyatt House Shelton

17. Days Inn by Wyndham Southington

18. Quality Inn Waterbury East

19. Hyatt Place Milford / New Haven

20. Residence Inn by Marriott Southington

Where to stay in Middlebury

Middlebury Center Historic District

Stay near popular Middlebury attractions

Quassy Amusement Park

Learn more about Middlebury

Top Middlebury Hotel Reviews

New Haven Hotel

Hampton Inn & Suites New Haven - South - West Haven

Holiday Inn Express Southington by IHG

Comfort Inn & Suites Danbury-Bethel

Wyndham Southbury

La Quinta Inn & Suites by Wyndham New Haven

More cheap stays in Middlebury

Red Roof Inn Meriden

Holiday Inn Express Southington by IHG

Microtel Inn & Suites by Wyndham Bethel/Danbury

Extended Stay America Suites Shelton Fairfield County

Best Western Executive Hotel Of New Haven - West Haven

Comfort Inn & Suites Danbury-Bethel

Hotels in Middlebury with star rating

Frequently asked questions

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