Middlebury Holiday Rentals, Connecticut: Private House Rentals

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Waterpark

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Our top choices for Middlebury hotels

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

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

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

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

1. Wyndham Southbury

Southbury

Catherine

Rp1.561.142

Rp1.795.314 total

includes taxes & fees

27 Oct - 28 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 courtyard with outdoor seating, stone walls, and a variety of plants.

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

2. Heritage Hotel, Golf & Conference Center

Southbury

anthony

Rp1.935.671

Rp2.534.849 total

includes taxes & fees

5 Oct - 6 Oct

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

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

A gym with treadmills, dumbbells, and exercise balls.

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

3. Hampton Inn Waterbury

Waterbury

Robert

Rp2.115.239

Rp2.432.525 total

includes taxes & fees

4 Oct - 5 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 hotel room with a large bed, a desk with a computer, a chair, and a small table.

4. Courtyard by Marriott Waterbury Downtown

Waterbury

Ludim

Rp1.772.397

Rp2.038.257 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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.

5. Holiday Inn Express Southington by IHG

Southington

Maria

Rp1.643.495

Rp1.890.020 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 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.

6. Days Inn by Wyndham Southington

Southington

Joselito

Rp1.593.367

Rp1.832.372 total

includes taxes & fees

29 Sept - 30 Sept

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

A swimming pool with lounge chairs and umbrellas, surrounded by a building with multiple windows.

A hotel room with a sofa, ottoman, bedside table, lamp, air conditioning unit, and a painting on the wall.

A reception desk with a digital display, a potted plant, and a sign that reads 'eat. drink. play.'

7. La Quinta Inn & Suites by Wyndham Danbury

Danbury

Steven

Rp2.076.741

Rp2.388.249 total

includes taxes & fees

11 Oct - 12 Oct

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

A hotel room with a bed, a desk with a computer, a microwave, a small fridge, a chair, and a large window with curtains.

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.

8. Fairfield by Marriott Inn & Suites Wallingford New Haven

Wallingford

samuel

Rp2.400.792

Rp2.760.911 total

includes taxes & fees

4 Oct - 5 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.

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

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

9. Holiday Inn Cheshire - Southington by IHG

Southington

Summer

Rp2.023.039

Rp2.326.494 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 spacious lobby with multiple seating areas, a large flat-screen TV, and a fireplace.

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

10. Residence Inn by Marriott New Haven Hamden

Hamden

Andrea

Rp2.578.032

Rp2.964.737 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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

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

11. Residence Inn by Marriott Southington

Southington

Mary

Rp3.043.510

Rp3.500.036 total

includes taxes & fees

18 Oct - 19 Oct

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

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

An indoor swimming pool with clear blue water, surrounded by chairs and potted plants, and a high ceiling with recessed lighting.

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

12. Clarion Inn North Haven - New Haven North

North Haven

Carol

Rp2.078.538

Rp2.390.318 total

includes taxes & fees

11 Oct - 12 Oct

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

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

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

A modern lounge area with a sofa and two armchairs, a coffee table, and a wall with a black and white abstract design.

13. Hampton Inn Danbury

Danbury

Donald

Rp2.571.766

Rp2.957.531 total

includes taxes & fees

4 Oct - 5 Oct

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

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

14. Homewood Suites by Hilton Southington, CT

Southington

Stephenie

Rp2.627.802

Rp3.021.972 total

includes taxes & fees

25 Oct - 26 Oct

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

A hotel room with two beds, a nightstand with a lamp, and framed artwork on the wall.

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.

15. Quality Inn Waterbury East

Waterbury

Wilfred

Rp1.658.713

Rp1.907.520 total

includes taxes & fees

5 Oct - 6 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 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.

16. Cheshire Welcome Inn

Cheshire

Kerem

Rp1.595.157

Rp1.834.430 total

includes taxes & fees

29 Sept - 30 Sept

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

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

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

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

17. DoubleTree by Hilton Hotel Bristol, Connecticut

Bristol

DARRON

Rp2.921.412

Rp3.359.624 total

includes taxes & fees

4 Oct - 5 Oct

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 modern lobby with leather sofas, a wooden reception desk, and a large abstract art piece on the wall.

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

18. Hyatt Place Milford / New Haven

Milford

Coran

Rp2.112.554

Rp2.429.437 total

includes taxes & fees

12 Oct - 13 Oct

A spacious foyer with a grand staircase, a chandelier, and a patterned carpet.

A well-lit room with a fireplace, two armchairs, a sofa, and a coffee table.

A well-lit living room with a patterned sofa, armchairs, a television, and a patterned carpet.

A spacious lobby with a patterned rug, a potted plant, and a television.

19. The Farmington Inn & Suites

Farmington

Brian

Rp3.025.607

Rp3.788.275 total

includes taxes & fees

30 Sept - 1 Oct

A hotel room with two beds, a desk, a chair, and a window with curtains.

A two-story motel with a central patio and a parking lot.

A bathroom with three sinks, a large mirror, and a door leading to another room.

A hotel room with a TV mounted on the wall displaying a sports game, a small refrigerator, a microwave, and a coffee maker on a shelf.

20. Rocky River Inn

New Milford

Nancy

Rp2.309.487

Rp2.655.910 total

includes taxes & fees

29 Sept - 30 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

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent

"Always a great stay!! Thank you for always being nice and helpful!"

New Haven Hotel

10/10 Excellent

"Very nice hotel in the heart of New Haven. Good clean rooms, great location, good parking. No free breakfast but plenty of good places nearby."

Hilton Garden Inn Shelton

10/10 Excellent

"Staff was very friendly. Location is great for Sacred Heart parents"

Hotel Marcel New Haven, Tapestry Collection By Hilton

10/10 Excellent

"The parking setup is a bit odd but the hotel, rooms, restaurant/bar, and staff were truly fantastic."

Hyatt Place Milford / New Haven

10/10 Excellent

"Nice clean room"

Red Roof Inn Meriden

10/10 Excellent

"No comments"

More cheap stays in Middlebury

Red Roof Inn Meriden

10 Bee St Meriden CT

Rp1.530.527

Rp1.760.044 total

29 Sept - 30 Sept

includes taxes & fees

7.6/10 Good! (1,005 reviews)

Holiday Inn Express Southington by IHG

120 Laning St Southington CT

Rp1.643.495

Rp1.890.020 total

4 Oct - 5 Oct

includes taxes & fees

Best Western Executive Hotel Of New Haven - West Haven

490 Saw Mill Rd West Haven CT

Rp1.963.064

Rp2.257.524 total

7 Oct - 8 Oct

includes taxes & fees

8.2/10 Very good! (1,862 reviews)

Comfort Inn & Suites Danbury-Bethel

80 Newtown Road Danbury CT

Rp1.990.814

Rp2.289.436 total

25 Oct - 26 Oct

includes taxes & fees

8.4/10 Very good! (895 reviews)

Microtel Inn & Suites by Wyndham Bethel/Danbury

80 Benedict Rd Bethel CT

Rp2.094.651

Rp2.408.849 total

1 Oct - 2 Oct

includes taxes & fees

Hampton Inn & Suites New Haven - South - West Haven

510 Saw Mill Rd West Haven CT

Rp2.267.415

Rp2.607.527 total

18 Oct - 19 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 Rp1.214.719

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. Wyndham Southbury

2. Heritage Hotel, Golf & Conference Center

3. Hampton Inn Waterbury

4. Courtyard by Marriott Waterbury Downtown

5. Holiday Inn Express Southington by IHG

6. Days Inn by Wyndham Southington

7. La Quinta Inn & Suites by Wyndham Danbury

8. Fairfield by Marriott Inn & Suites Wallingford New Haven

9. Holiday Inn Cheshire - Southington by IHG

10. Residence Inn by Marriott New Haven Hamden

11. Residence Inn by Marriott Southington

12. Clarion Inn North Haven - New Haven North

13. Hampton Inn Danbury

14. Homewood Suites by Hilton Southington, CT

15. Quality Inn Waterbury East

16. Cheshire Welcome Inn

17. DoubleTree by Hilton Hotel Bristol, Connecticut

18. Hyatt Place Milford / New Haven

19. The Farmington Inn & Suites

20. Rocky River Inn

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

Best Western Executive Hotel Of New Haven - West Haven

New Haven Hotel

Hilton Garden Inn Shelton

Hotel Marcel New Haven, Tapestry Collection By Hilton

Hyatt Place Milford / New Haven

Red Roof Inn Meriden

More cheap stays in Middlebury

Red Roof Inn Meriden

Holiday Inn Express Southington by IHG

Best Western Executive Hotel Of New Haven - West Haven

Comfort Inn & Suites Danbury-Bethel

Microtel Inn & Suites by Wyndham Bethel/Danbury

Hampton Inn & Suites New Haven - South - West Haven

Frequently asked questions

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