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Featured Cottages in Middlebury

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

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

West Haven CT
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.
Cozy 2-bedroom Cottage with Access to Bantam Lake

Cozy 2-bedroom Cottage with Access to Bantam Lake

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

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

Plymouth CT
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

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

Charming Connecticut Retreat Near Museums & Hiking

3 out of 5
Waterbury CT
Guests of this cottage have access to free WiFi in public areas. Free parking is available if you drive.
Lakefront Home, Close to Mt Southington!

Lakefront Home, Close to Mt Southington!

3 out of 5
1743 Meriden Rd Wolcott CT
This cottage features free WiFi in public areas and barbecue grills. Free parking is included with your stay.
Squantz Pond Oasis, charming cottage, Firepit and lake view

Squantz Pond Oasis, charming cottage, Firepit and lake view

New Fairfield CT
At this cottage, guests have access to features like laundry facilities.
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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

    New Haven Hotel

    New Haven Hotel

    229 George Street New Haven CT
    $106 nightly
    The price is $122 total per night from Jan 13 to Jan 14
    $122 total
    Jan 13 - Jan 14
    Total with taxes and fees
    9/10 Wonderful! (1,978 reviews)
    Cambria Hotel New Haven University Area

    Cambria Hotel New Haven University Area

    20 Dwight Street New Haven CT
    $103 nightly
    The price is $119 total per night from Jan 25 to Jan 26
    $119 total
    Jan 25 - Jan 26
    Total with taxes and fees
    8.6/10 Excellent! (1,004 reviews)
    Hampton Inn by Hilton Shelton

    Hampton Inn by Hilton Shelton

    695 Bridgeport Ave Shelton CT
    $106 nightly
    The price is $122 total per night from Jan 8 to Jan 9
    $122 total
    Jan 8 - Jan 9
    Total with taxes and fees
    8.6/10 Excellent! (1,003 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
$119
Highest Price
$122
Popular accommodation
Modern 4 Bedroom Beach House: Ideal for Families & Long Stays, Cozy 2-bedroom Cottage with Access to Bantam Lake, Cozy cottage with AC and lake access in charming Connecticut suburb., 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, Lakefront Home, Close to Mt Southington!, Squantz Pond Oasis, charming cottage, Firepit and lake view

More to Explore