Middlebury Holiday Rentals, Connecticut: Private House Rentals

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Our top choices for Middlebury hotels

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.

1. Hampton Inn Waterbury

Waterbury

Christina

฿3,913

฿4,500 total

includes taxes & fees

1 Oct - 2 Oct

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

A hotel lobby with a seating area featuring sofas, armchairs, and ottomans.

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

2. Courtyard by Marriott Waterbury Downtown

Waterbury

Ludim

฿2,948

฿3,390 total

includes taxes & fees

27 Sept - 28 Sept

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

An indoor swimming pool with blue walls, a skylight, and lounge chairs.

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.

3. Wyndham Southbury

Southbury

Catherine

฿2,915

฿3,352 total

includes taxes & fees

25 Oct - 26 Oct

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

A hotel breakfast area with a buffet setup, including a coffee machine, fruit juice dispenser, and various food items.

4. Comfort Inn Naugatuck-Shelton, CT

Naugatuck

Denny

฿3,138

฿3,608 total

includes taxes & fees

18 Oct - 19 Oct

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.

5. Heritage Hotel, Golf & Conference Center

Southbury

Zuleika

฿3,614

฿4,733 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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.

6. Quality Inn Waterbury East

Waterbury

Wilfred

฿3,069

฿3,529 total

includes taxes & fees

1 Oct - 2 Oct

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

A modern restaurant with a wooden bar area, a long table with chairs, and a menu board.

A modern bar area with a white countertop, three brown bar stools, a mounted TV, and a liquor display cabinet.

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

7. Holiday Inn Cheshire - Southington by IHG

Southington

Summer

฿3,643

฿4,190 total

includes taxes & fees

25 Oct - 26 Oct

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

A modern kitchen with a marble backsplash, stainless steel appliances, and dark cabinetry.

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

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

8. Residence Inn by Marriott New Haven Hamden

Hamden

Andrea

฿4,980

฿5,727 total

includes taxes & fees

4 Oct - 5 Oct

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 modern interior with a seating area, a counter, and large windows.

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

9. Days Inn by Wyndham Southington

Southington

Sheryl

฿2,948

฿3,390 total

includes taxes & fees

27 Sept - 28 Sept

A compact hotel room with a kitchenette, a bed, and a view of the outdoors.

A hotel room with a bed, a chair, a small table with a plant, and a mirror.

A modern building with a sign reading 'LA QUINTA' and a landscaped area with a tree and flowers.

A swimming pool with lounge chairs and a lifebuoy on the fence.

10. La Quinta Inn & Suites by Wyndham Danbury

Danbury

Eduardo

฿3,794

฿4,363 total

includes taxes & fees

27 Sept - 28 Sept

A hotel room with a large bed, two bedside tables with lamps, and a striped wall.

A Keurig coffee maker with a cup of coffee and several coffee pods on a tray.

A hotel bathroom with a large mirror, a vanity with drawers, a sink, and a towel rack.

A covered porch with white columns and black hanging lanterns.

11. The Milestone Inn

Woodbury

KEITH

฿3,547

฿4,080 total

includes taxes & fees

5 Oct - 6 Oct

A hallway with a purple-lit wall, patterned red wall, and a ceiling with recessed lighting.

A motel entrance with a doormat reading "Waterbury Big Apple Motel," a large window with a view of parked cars, and a small American flag.

A motel with a neon sign, a staircase, and a parked vehicle.

A compact hotel room with a kitchenette, a dining area with a table and chairs, and a large mirror.

12. Waterbury Motel

Waterbury

Jason

฿1,954

฿2,247 total

includes taxes & fees

25 Sept - 26 Sept

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

A spacious lobby with a stone wall, seating areas, a fireplace, and a kitchen in the background.

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

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

13. Homewood Suites by Hilton Southington, CT

Southington

Stephenie

฿5,337

฿6,137 total

includes taxes & fees

5 Oct - 6 Oct

A hotel room with a large bed, a wooden nightstand, a TV, and a bathroom visible through an open door.

A hotel room with a wooden desk, a chair, a flat-screen TV, a framed picture, and a window with curtains.

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

A conference room with multiple tables and chairs, a whiteboard, and a projector screen.

14. Holiday Inn Express Southington by IHG

Southington

Maria

฿3,041

฿3,497 total

includes taxes & fees

4 Oct - 5 Oct

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 spacious room with a fireplace, a large dining table, multiple chairs, and a television mounted on the wall.

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

15. Residence Inn by Marriott Southington

Southington

Mary

฿5,381

฿6,189 total

includes taxes & fees

4 Oct - 5 Oct

An indoor swimming pool with clear blue water, surrounded by lounge chairs and a large window with a forest view.

A snack display with various chips and snacks, a refrigerated beverage area, and framed pictures on the wall.

A hot tub with a view of trees through large windows.

A Hampton Inn hotel with a modern design, featuring a central entrance, multiple floors, and a parking lot.

16. Hampton Inn Danbury

Danbury

Donald

฿4,802

฿5,522 total

includes taxes & fees

4 Oct - 5 Oct

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

A lobby with a leather sofa, a reception desk, framed pictures on the wall, and a door.

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

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

17. Cheshire Welcome Inn

Cheshire

Melissa

฿2,978

฿3,425 total

includes taxes & fees

28 Sept - 29 Sept

An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.

A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a reception area.

A modern lobby with a reception desk, seating area, and a large decorative light fixture.

A modern hotel lobby with a central island, red chairs, a marble countertop, and a large overhead light fixture.

18. DoubleTree by Hilton Hotel Bristol, Connecticut

Bristol

DARRON

฿5,399

฿6,209 total

includes taxes & fees

18 Oct - 19 Oct

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

A living room with a beige wall, a glass coffee table, two leather sofas, a small table with a vase of flowers, and a painting of a blue sky and trees.

A hotel reception area with a wooden reception desk, a black and white doormat, and a large window with a view of greenery.

A room with a desk, a blue sofa, a window with curtains, and a radiator.

19. Econo Lodge Bethel - Danbury

Bethel

Alexander

฿3,304

฿3,799 total

includes taxes & fees

27 Sept - 28 Sept

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

A room with a dining table, four wooden stools, a window with blinds, and a view of the outside.

A modern dining area with white tables and chairs, a counter with a coffee machine, and a blue accent wall.

A modern hotel room with a dining area, a TV, and a large window with curtains.

20. Microtel Inn & Suites by Wyndham Bethel/Danbury

Bethel

nelson

฿3,577

฿4,114 total

includes taxes & fees

27 Sept - 28 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.

See properties

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.

See properties

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

Wyndham Southbury

8/10 Good

"Extra for microwave in room so if you want one be sure to book with it."

New Haven Hotel

8/10 Good

"The room was clean and the hotel staff was OK. Parking is extra and located across the street. The downtown area that it situated down is nice and has some amenities. I wouldn’t stay here for a vacation but for a business trip it’s OK and serve the purpose Nicely as a business traveler looks for 9+ properties. This one fits at a nine."

Hilton Garden Inn Milford

10/10 Excellent

"Great stay"

Hyatt Place Milford / New Haven

10/10 Excellent

"I love the fresh cut up fruits for breakfast. Microwave is not available in our room. The electrical socket near the tv was not working. Construction noises woke me up. Other than those small little things everything was perfect."

Comfort Inn & Suites Danbury-Bethel

10/10 Excellent

"Nice room darkening blinds. Great hot breakfast. Comfy, motion-separation mattress!"

Hilton Garden Inn Shelton

10/10 Excellent

"Smelled clean, clean rooms and property, nice staff."

More cheap stays in Middlebury

Red Roof Inn Meriden

10 Bee St Meriden CT

฿2,832

฿3,256 total

27 Sept - 28 Sept

includes taxes & fees

7.4/10 Good! (1,002 reviews)

Holiday Inn Express Southington by IHG

120 Laning St Southington CT

฿3,041

฿3,497 total

4 Oct - 5 Oct

includes taxes & fees

Microtel Inn & Suites by Wyndham Bethel/Danbury

80 Benedict Rd Bethel CT

฿3,577

฿4,114 total

27 Sept - 28 Sept

includes taxes & fees

8.2/10 Very good! (1,005 reviews)

Best Western Executive Hotel Of New Haven - West Haven

490 Saw Mill Rd West Haven CT

฿3,632

฿4,176 total

7 Oct - 8 Oct

includes taxes & fees

Comfort Inn & Suites Danbury-Bethel

80 Newtown Road Danbury CT

฿3,717

฿4,274 total

25 Oct - 26 Oct

includes taxes & fees

8.4/10 Very good! (889 reviews)

Hampton Inn & Suites New Haven - South - West Haven

510 Saw Mill Rd West Haven CT

฿4,233

฿4,868 total

25 Oct - 26 Oct

includes taxes & fees

Frequently asked questions

What's the best place for a stay in Middlebury?

Located 18.5 mi (29.8 km) from the heart of Middlebury, New Haven Hotel is a top choice for your stay, based on our traveller data. Other good options for your trip to the area are Holiday Inn Express Southington by IHG and Best Western Executive Hotel Of New Haven - West Haven. See all available top hotels, or vacation rentals in Middlebury.

If I need to cancel my hotel reservation in Middlebury, will I receive a refund?

Yes, most hotel reservations are fully refundable provided that you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you have a non-refundable reservation, it might still be possible to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Middlebury.

What's it like staying in Middlebury?

Visitors can enjoy all that Middlebury has to offer, including its parks. There are 1098 hotels and other accommodation options in the surrounding area. Find out more about Middlebury.

What should I do while I'm visiting Middlebury?

A couple of favourite places to visit are Quassy Amusement Park and Lake Quassapaug. You'll also find Palace Theatre and Beacon Falls Town Recreation Field in the area. Take a look at what more there is to see and do in Expedia's Middlebury guide.

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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Book Hotels in Middlebury on Expedia.com

Find hotels in Middlebury, CT from ฿2,247

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. Hampton Inn Waterbury

2. Courtyard by Marriott Waterbury Downtown

3. Wyndham Southbury

4. Comfort Inn Naugatuck-Shelton, CT

5. Heritage Hotel, Golf & Conference Center

6. Quality Inn Waterbury East

7. Holiday Inn Cheshire - Southington by IHG

8. Residence Inn by Marriott New Haven Hamden

9. Days Inn by Wyndham Southington

10. La Quinta Inn & Suites by Wyndham Danbury

11. The Milestone Inn

12. Waterbury Motel

13. Homewood Suites by Hilton Southington, CT

14. Holiday Inn Express Southington by IHG

15. Residence Inn by Marriott Southington

16. Hampton Inn Danbury

17. Cheshire Welcome Inn

18. DoubleTree by Hilton Hotel Bristol, Connecticut

19. Econo Lodge Bethel - Danbury

20. Microtel Inn & Suites by Wyndham Bethel/Danbury

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

Wyndham Southbury

New Haven Hotel

Hilton Garden Inn Milford

Hyatt Place Milford / New Haven

Comfort Inn & Suites Danbury-Bethel

Hilton Garden Inn Shelton

More cheap stays in Middlebury

Red Roof Inn Meriden

Holiday Inn Express Southington by IHG

Microtel Inn & Suites by Wyndham Bethel/Danbury

Best Western Executive Hotel Of New Haven - West Haven

Comfort Inn & Suites Danbury-Bethel

Hampton Inn & Suites New Haven - South - West Haven

Frequently asked questions

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