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Featured Middlebury Cottages

Cozy cottage with AC and lake access in charming Connecticut suburb.

Cozy cottage with AC and lake access in charming Connecticut suburb.

Watertown, CT
This cottage features a water park and barbecue grills.
Modern 4 Bedroom Beach House: Ideal for Families & Long Stays

Modern 4 Bedroom Beach House: Ideal for Families & Long Stays

Guests staying at this cottage enjoy a gym, an arcade/game room, and laundry facilities. Helpful staff is there to provide concierge services, as well as offer insight about the area. Other amenities at this family-friendly cottage include local meal delivery service, a garden, and barbecue grills.
Charming, private 2-bedroom cottage on classic New England farm in Washington CT

Charming, private 2-bedroom cottage on classic New England farm in Washington CT

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Cozy 2-bedroom Cottage with Access to Bantam Lake

Cozy 2-bedroom Cottage with Access to Bantam Lake

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT

Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT

At this cottage, guests have access to a gym, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

Guests of this cottage enjoy access to a water park, laundry facilities, and a garden. This family-friendly cottage also has barbecue grills.
Historic Whitneyville Cottage

Historic Whitneyville Cottage

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Charming Connecticut Retreat Near Museums & Hiking

Charming Connecticut Retreat Near Museums & Hiking

3 out of 5
Guests of this cottage have access to free WiFi in public areas. Free parking is available if you drive.
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC

Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
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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.

Hotel Options in Middlebury

    Trumbull Marriott Shelton

    Trumbull Marriott Shelton

    180 Hawley Ln, Trumbull, CT
    $139 nightly
    The price is $160 total per night from Oct 26 to Oct 27
    $160 total
    Oct 26 - Oct 27
    Total with taxes and fees
    8/10 Very Good! (1,000 reviews)
    Omni New Haven Hotel at Yale

    Omni New Haven Hotel at Yale

    155 Temple St, New Haven, CT
    $167 nightly
    The price is $192 total per night from Oct 19 to Oct 20
    $192 total
    Oct 19 - Oct 20
    Total with taxes and fees
    8.4/10 Very Good! (1,016 reviews)
    New Haven Hotel

    New Haven Hotel

    229 George Street, New Haven, CT
    $119 nightly
    The price is $137 total per night from Oct 26 to Oct 27
    $137 total
    Oct 26 - Oct 27
    Total with taxes and fees
    9/10 Wonderful! (1,811 reviews)

Cottages

Book a cottage in Middlebury
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Middlebury. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Middlebury better.

Cottage apartments in Middlebury range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Middlebury
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Middlebury and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Middlebury cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Middlebury. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Middlebury Cottages essential information

Accommodation
53 Cottages
Lowest Price
$137
Highest Price
$192
Popular accommodation
Cozy cottage with AC and lake access in charming Connecticut suburb., Modern 4 Bedroom Beach House: Ideal for Families & Long Stays, Charming, private 2-bedroom cottage on classic New England farm in Washington CT, Cozy 2-bedroom Cottage with Access to Bantam Lake, Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT, Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape, Historic Whitneyville Cottage, Charming Connecticut Retreat Near Museums & Hiking, Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC

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