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Find 5 Star Hotels in Middlebury, CT from $160

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Check availability on Middlebury 5 Star Hotels

Tonight
Sep 26 - Sep 27
Tomorrow
Sep 27 - Sep 28
Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11

Our top choices for Middlebury 5-star hotels

A covered porch with wicker furniture, a table with drinks, and potted plants.
A dining area with wicker chairs, a patterned floor, and wall-mounted decorative plates.
A room with patterned wallpaper, a chandelier, a round table with stools, a fireplace, and a large plant.
A large indoor swimming pool with clear blue water, surrounded by white walls and large windows.

1. Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection
Washington
United States
Angela
$1,297 nightly
$1,492 total
Oct 4 - Oct 5
Total with taxes and fees
Mayflower Inn & Spa, Auberge Collection
A large, two-story house with a wrap-around porch, a central entrance, and a flag.
A dining area with a round table, chairs, a fireplace, and a variety of plants.
A spacious living room with a large sectional sofa, a round coffee table, and a chandelier. There are large windows with curtains, a fireplace, and a view of greenery outside.
A modern house with a white exterior, two wooden doors, and a grey awning.

2. Belden House & Mews

Belden House & Mews
Litchfield Historic District
United States
Mj
$523 nightly
$601 total
Sep 27 - Sep 28
Total with taxes and fees
Belden House & Mews
A hot tub in a backyard with a house, trees, and a clear sky.
A living room with a sofa, ottoman, glass coffee table, and a patterned rug. There are two lamps, a decorative statue, and a framed artwork on the wall.
A spacious living room with a dining area, large windows, and a chandelier.
A hot tub with a wicker basket, lounge chairs, and a barbecue grill in a backyard.

3. Las Flores Villa

Las Flores Villa
New Preston
$3,348 nightly
$3,850 total
Oct 1 - Oct 2
Total with taxes and fees
Las Flores Villa
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Middlebury.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

155 Temple St New Haven CT
$151 nightly
$174 total
Oct 26 - Oct 27
Total with taxes and fees
Omni New Haven Hotel at Yale
The Blake Hotel

The Blake Hotel

9 High Street New Haven CT
$211 nightly
$242 total
Sep 27 - Sep 28
Total with taxes and fees
9.4/10 Exceptional! (1,002 reviews)
The Blake Hotel
Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton

500 Sargent Drive New Haven CT
$139 nightly
$160 total
Oct 26 - Oct 27
Total with taxes and fees
9.4/10 Exceptional! (1,008 reviews)
Hotel Marcel New Haven, Tapestry Collection By Hilton
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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.
Photo by Brandon Miller

Top Middlebury Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Middlebury?
You'll find a range of pricing options for 5-star hotels in Middlebury on Expedia. How much you'll pay will depend on your vacation dates, length of your trip and other factors. Compare all of the available properties for your preferred dates and use our pricing and other filters to discover the ideal high-end stay.
  • Search for the lowest price per night from $160
What makes a hotel 5 stars in Middlebury?
Flawless guest service is the hallmark of every 5-star hotel in Middlebury. From the moment you arrive, staff cater to your every need, whether arranging valet parking or providing in-room massages. Plus, hotels must feature superior amenities to obtain a 5-star rating. These can include deluxe baths, saunas or spas, swimming pools, gourmet kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Middlebury?
Our convenient filters are the easiest way to search for exactly what you're looking for. Select "5-star" and "All inclusive" to see the most upscale properties in Middlebury where your meals, accommodations, entertainment and activities are included in the price. At these retreats, your vacation is pure leisure from the moment you put down your suitcase.

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