Hotels in Middlebury

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Top 5 hotels in Middlebury at a glance

Wyndham Southbury — 3-star hotel in Southbury. Guest rating: 8.2/10 — Very Good.
Hampton Inn Waterbury — 2.5-star hotel in Waterbury. Guest rating: 8.2/10 — Very Good.
Courtyard by Marriott Waterbury Downtown — 3-star hotel in Waterbury. Guest rating: 8.4/10 — Very Good.
Heritage Hotel, Golf & Conference Center — 3.5-star hotel in Southbury. Guest rating: 8.4/10 — Very Good.
Comfort Inn Naugatuck-Shelton, CT — 2.5-star hotel in Naugatuck. Guest rating: 8.0/10 — Very Good.

Where to stay in Middlebury?

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

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

Wyndham Southbury

Southbury

$93

$107 total

includes taxes & fees

Sep 20 - Sep 21

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 reception desk with a wooden finish, a digital screen, and a large poster on the wall.

Hampton Inn Waterbury

Waterbury

$118

$136 total

includes taxes & fees

Sep 7 - Sep 8

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.

Courtyard by Marriott Waterbury Downtown

Waterbury

$89

$102 total

includes taxes & fees

Sep 6 - Sep 7

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

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

A courtyard with outdoor seating, stone walls, and a variety of plants.

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

Heritage Hotel, Golf & Conference Center

Southbury

$125

$161 total

includes taxes & fees

Sep 8 - Sep 9

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.

Comfort Inn Naugatuck-Shelton, CT

Naugatuck

$97

$112 total

includes taxes & fees

Sep 13 - Sep 14

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

A covered porch with white columns and black hanging lanterns.

A neatly made bed with white linens, a white bedside table with a lamp, and a telephone.

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

The Milestone Inn

Woodbury

$107

$123 total

includes taxes & fees

Sep 7 - Sep 8

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

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

Quality Inn Waterbury East

Waterbury

$93

$107 total

includes taxes & fees

Sep 7 - Sep 8

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

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

Waterbury Motel

Waterbury

$59

$68 total

includes taxes & fees

Sep 2 - Sep 3

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

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

Cheshire Welcome Inn

Cheshire

$84

$97 total

includes taxes & fees

Sep 2 - Sep 3

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

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

Holiday Inn Cheshire - Southington by IHG

Southington

$114

$131 total

includes taxes & fees

Sep 7 - Sep 8

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

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.

Holiday Inn Express Southington by IHG

Southington

$88

$102 total

includes taxes & fees

Sep 13 - Sep 14

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

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.

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

Days Inn by Wyndham Southington

Southington

$88

$101 total

includes taxes & fees

Oct 1 - Oct 2

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

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

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

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

Homewood Suites by Hilton Southington, CT

Southington

$139

$159 total

includes taxes & fees

Sep 7 - Sep 8

A motel lobby with a reception desk, a television mounted above it, a large window offering a view of the parking lot and trees, and a potted plant near the window.

A hotel room with a bed, a desk, a chair, a TV, a mirror, and a bathroom visible through an open door.

A building with a 'welcome' sign and a 'Penny's Diner' sign.

A small room with a window, a television, a coffee machine, a potted plant, and a chair.

Motel 6 Southington, CT - Hartford

Southington

$70

$80 total

includes taxes & fees

Sep 3 - Sep 4

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

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

Microtel Inn & Suites by Wyndham Bethel/Danbury

Bethel

$104

$120 total

includes taxes & fees

Sep 29 - Sep 30

A modern lobby with a high ceiling, brick walls, and a glass enclosure. There are seating areas with tables and chairs, and a kitchen area in the background.

A hotel with a modern design, featuring a prominent 'Best Western' sign, large windows, and a well-lit entrance.

A room with a blue textured wall, two computer monitors, a desk, two chairs, and a small plant.

A hotel room with a large bed, a desk with a computer, a television, and a window with curtains.

Best Western Danbury/Bethel

Bethel

$106

$121 total

includes taxes & fees

Sep 14 - Sep 15

A hotel room with two beds, a nightstand with a lamp, and a wall-mounted phone.

A bathroom with a shower, toilet, and towel rack.

A hotel room with a kitchenette, a desk, a chair, a mirror, and a door.

PLYMOUTH MOTOR LODGE

Terryville

$89

$102 total

includes taxes & fees

Sep 2 - Sep 3

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

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

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

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

Clarion Inn North Haven - New Haven North

North Haven

$107

$123 total

includes taxes & fees

Sep 27 - Sep 28

A busy bar area with multiple screens displaying content, wooden decor, and a crowd of people.

A bar area with multiple VANS branded signs, wooden bar counter, and several bar stools.

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

A modern building with a sign reading 'LAQUINTA' and a landscaped area with a small tree.

La Quinta Inn & Suites by Wyndham Danbury

Danbury

$115

$132 total

includes taxes & fees

Sep 20 - Sep 21

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.

A hotel lobby with a round dining table, several chairs, a reception desk, and a patterned carpet.

Danbury Inn & Suites

Danbury

$115

$132 total

includes taxes & fees

Sep 2 - Sep 3

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Go beyond your typical stay in Middlebury

Pet friendly

Apartment

Pool

Hot tub

Cottage

Family friendly

Top neighborhoods in Middlebury

Middlebury Center Historic District

Middlebury Center Historic District

Middlebury's Middlebury Center Historic District neighborhood offers attractions including Lake Quassapaug.

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Top landmarks in Middlebury

Quassy Amusement Park

8.2/10 (21 reviews)

Why not give yourself a treat with a trip to Quassy Amusement Park, one of the family attractions located 1.2 mi (1.9 km) from central Middlebury. If you have fun at Quassy Amusement Park, you'll love Glebe House Museum and The Gertrude Jekyll Garden, located nearby.

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Learn more about Middlebury

Middlebury is well-known for its attractions such as Quassy Amusement Park and Lake Quassapaug.

See all hotels in Middlebury

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

Check out reviews of Middlebury hotels guests love

Cambria Hotel New Haven University Area

10/10 Excellent

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Courtyard by Marriott Waterbury Downtown

10/10 Excellent

"I enjoyed my stay. I will definitely stay there again."

Holiday Inn Express Southington by IHG

10/10 Excellent

"Very clean place. And staff was amazing"

Hampton Inn & Suites New Haven - South - West Haven

10/10 Excellent

"Excellent, convenient and quiet."

Best Western Executive Hotel Of New Haven - West Haven

8/10 Good

"The room was clean but the carpet was stained in places, and the bed was very comfortable. I did not utilize the pool or the breakfast so I can’t comment on them. There is not a lot of parking in the front of the building and didn’t feel safe parking in back at night. I feel it was a good value for the money."

Omni New Haven Hotel at Yale

10/10 Excellent

"Just a great hotel"

New Haven Hotel

10/10 Excellent

"Great location. Well presented. Good size room. Staff were very helpful"

Courtyard by Marriott New Haven Orange-Milford

8/10 Good

"Air Conditioner was very loud."

Hotel Marcel New Haven, Tapestry Collection By Hilton

10/10 Excellent

"Breakfast was excellent with reasonable price"

Frequently asked questions

What hotels do travelers like in Middlebury?

Guests like Wyndham Southbury, Courtyard by Marriott Waterbury Downtown and Heritage Hotel, Golf & Conference Center.

Can I book refundable hotels in Middlebury?

If you need the flexibility to change your plans to Middlebury, most properties provide refundable* rates you can book. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.

What will the weather in Middlebury be like during my vacation?

The warmest months in Middlebury are usually July and August with an average temp of 69°F. January and February are the chilliest months when the average temp is 32°F. The rainiest months are October and July.

Why should I book my Middlebury accommodation with Hotels.com?

There are plenty of reasons to book your Middlebury travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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