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Featured Cottages in Middlebury

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

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

Watertown CT
At this cottage, guests have access to barbecue grills.
Cozy 2-bedroom cottage in peaceful Danbury with AC

Cozy 2-bedroom cottage in peaceful Danbury with AC

Danbury CT
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
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, barbecue grills, and a garden.
Escape to Bantam Lake. Waterfront!

Escape to Bantam Lake. Waterfront!

Morris CT
Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Cozy Lake Community Cottage with private beach & hot tub - ideal for long stays

Cozy Lake Community Cottage with private beach & hot tub - ideal for long stays

New Fairfield CT
At this cottage, guests have access to features like laundry facilities.
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, barbecue grills, and a garden.
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!

Lakeview property in private community. Lake & beach access. Swim/Kayak all day!

Bethlehem CT
Guests staying at this cottage have access to a garden and barbecue grills.
Historic Whitneyville Cottage

Historic Whitneyville Cottage

Hamden CT
Guests staying at this cottage have access to laundry facilities, a garden, 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.
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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 Apr 12 to Apr 13
    $122 total
    Apr 12 - Apr 13
    Total with taxes and fees
    9/10 Wonderful! (2,055 reviews)
    Holiday Inn Express Southington by IHG

    Holiday Inn Express Southington by IHG

    120 Laning St Southington CT
    $108 nightly
    The price is $124 total per night from Apr 12 to Apr 13
    $124 total
    Apr 12 - Apr 13
    Total with taxes and fees
    8.6/10 Excellent! (1,254 reviews)
    Hyatt Place Milford / New Haven

    Hyatt Place Milford / New Haven

    190 Old Gate Lane Milford CT
    $110 nightly
    The price is $126 total per night from Apr 5 to Apr 6
    $126 total
    Apr 5 - Apr 6
    Total with taxes and fees
    8.6/10 Excellent! (1,288 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
$122
Highest Price
$126
Popular accommodation
Cozy cottage with AC and lake access in charming Connecticut suburb., Cozy 2-bedroom cottage in peaceful Danbury with AC, Modern 4 Bedroom Beach House: Ideal for Families & Long Stays, Escape to Bantam Lake. Waterfront!, Cozy Lake Community Cottage with private beach & hot tub - ideal for long stays, Cozy 2-bedroom Cottage with Access to Bantam Lake, Lakeview property in private community. Lake & beach access. Swim/Kayak all day!, Historic Whitneyville Cottage, Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT

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