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Compare 51 Cottages in Woodbury with updated reviews, rates, and availability.

Peaceful Goshen Cottage w/ Screened Porch & Views!
Goshen Vacation Rental | 3BR | 1.5BA | 1,500 Sq Ft | Stairs Required for Entry
Peaceful Goshen Cottage w/ Screened Porch & Views!
9.0 out of 10, Wonderful, (29)
"Enjoyed our stay very much. The accommodations suited our needs. Appreciated the cleanliness of the property and the ease of checking in/out."
Peaceful Goshen Cottage w/ Screened Porch & Views!
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
Private Beach 100 yards from Cottage
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
9.4 out of 10, Exceptional, (86)
"Perfectly adorable house that was ideal for our brief getaway. I wish we had been able to use the kayak/canoe but time was tight. The only issue was the driveway which had me holding my breath a bit but luckily we were careful and managed without incident."
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
Newly renovated cottage on the lake!
Beach
Newly renovated cottage on the lake!
10.0 out of 10, Exceptional, (22)
"We love live live this property. It is perfect for what we need. Our daughter lives just a shirt distance away in Torrington. This is our second time staying in this house. We love it"
Newly renovated cottage on the lake!
Idillic summer getaway in Litchfield Hills, CT.
Property grounds
Idillic summer getaway in Litchfield Hills, CT.
10.0 out of 10, Exceptional, (13)
"The place was as described and very comfortable. We enjoyed our stay!"
Idillic summer getaway in Litchfield Hills, CT.
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
Property grounds
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
9.6 out of 10, Exceptional, (14)
"Landscaping was spectacular and we enjoyed a beautiful view of the lake. Baths and bedrooms very clean. Plenty of charging ports. Terrible mold and mildew smell in lower level. Number of hazards noted, handrail missing on stairs, no lights on outdoor stairway, thermostat access by leaning over the stairs. The property needs a good deep cleaning."
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
Cozy 2-bedroom Cottage with Access to Bantam Lake
Cozy 2-bedroom Cottage with Access to Bantam Lake
9.6 out of 10, Exceptional, (17)
"The lake and all the homes were beautiful and the house was very clean, organized, and felt like home. "
Cozy 2-bedroom Cottage with Access to Bantam Lake
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
Private Dock
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
10.0 out of 10, Exceptional, (5)
"Lovely little cottage right on the arm of the lake. Nicely appointed and updated, quiet and great for a couple. Nearby towns are adorable."
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Living area
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
3.0 star property
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Candlewood Lake Retreat with year round views
Exterior
Candlewood Lake Retreat with year round views
10.0 out of 10, Exceptional, (10)
"Liked outdoor area and fire place "
Candlewood Lake Retreat with year round views
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Fall sunsets are a prize possession here at the lake!
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
10.0 out of 10, Exceptional, (26)
"We stayed at the property for 2 nights and it was just what we had hoped. We enjoyed the lake, the fall colors and the house thoroughly. Would love to come back someday. "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Guest Cottage on Country Estate
Guest Cottage on 7 acre Estate. Two bedrooms, full bath with a laundry Sleeps 6
Guest Cottage on Country Estate
9.2 out of 10, Wonderful, (39)
"Quaint.Just the size for 2."
Guest Cottage on Country Estate
Historic Whitneyville Cottage
Exterior detail
Historic Whitneyville Cottage
9.6 out of 10, Exceptional, (12)
"Very convenient for what we needed. Nice little cottage."
Historic Whitneyville Cottage
Dainty New Preston Cottage w/ Dock & Lake Views!
Preston Vacation Rental | 3BR | 2BA | 1,300 Sq Ft | Stairs Required
Dainty New Preston Cottage w/ Dock & Lake Views!
9.0 out of 10, Wonderful, (33)
"We were in need of a nice, relaxing vacation and that’s exactly what we got. There were four of us (me, my husband, my 16-year-old, and my 11-year-old) and we each had our own space. We loved going down to the dock, and there is also a town beach just down the road. The home is filled with fun antiques and reminds you of a clean, well-kept, and charming grandmother’s house. We wanted a low-key vacation, and so we enjoyed short jaunts (less than 15 mins away) to Kent to enjoy its downtown and...
Dainty New Preston Cottage w/ Dock & Lake Views!
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Exterior
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
9.6 out of 10, Exceptional, (5)
"The house on the lake is clean and very cute. A few things to keep in mind… The stairs to the loft are VERY steep and VERY narrow. So both adults and small children may struggle to get up and down, especially with any type of luggage. There are no closets or dressers for your clothes so maybe bring hangers and a hook for behind the door. Everything else was perfect. "
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Modern, cozy 3 bedroom lakeside cottage
Exterior
Modern, cozy 3 bedroom lakeside cottage
10.0 out of 10, Exceptional, (5)
"House was perfect, well stocked and designed. Area was close to all Litchfield"
Modern, cozy 3 bedroom lakeside cottage
Charming Connecticut Retreat Near Museums & Hiking
Living area
Charming Connecticut Retreat Near Museums & Hiking
3.0 star property
Charming Connecticut Retreat Near Museums & Hiking
Wolcott Home w/ Deck: Near Connecticut Attractions
Living area
Wolcott Home w/ Deck: Near Connecticut Attractions
3.0 star property
Wolcott Home w/ Deck: Near Connecticut Attractions
Lakefront Home, Close to Mt Southington!
Outdoor dining
Lakefront Home, Close to Mt Southington!
3.0 star property
Lakefront Home, Close to Mt Southington!
Upscale Waterbury Retreat w/ Indoor Hot Tub!
Interior
Upscale Waterbury Retreat w/ Indoor Hot Tub!
3.0 star property
Upscale Waterbury Retreat w/ Indoor Hot Tub!
Modern Escape w/ Fire Pit, Near Lake Waramaug
Property grounds
Modern Escape w/ Fire Pit, Near Lake Waramaug
3.0 star property
Modern Escape w/ Fire Pit, Near Lake Waramaug
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.
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Other property types in Woodbury

Spacious Woodbury Home w/ Pool + Hot Tub!
Woodbury Vacation Rental | 4BR | 3BA | 3,321 Sq Ft | Stairs Required for Access
Spacious Woodbury Home w/ Pool + Hot Tub!
Spacious Woodbury Home w/ Pool + Hot Tub!
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Main deck w/ grill & sweeping lake views. Baby/dog gate at deck stairs.
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (73)
"Our group of 2 couples enjoyed our week in the Hudson Valley area. We all commented on the excellent beds and pillows, the view of the lake from the house and the quiet of the neighborhood. Would stay here again."
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Breathtaking lake views while grilling out and soaking up the sun with family!
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
9.4 out of 10, Exceptional, (14)
"This house does have a lovely view that allowed us to take in the changing leaves off the reflection of the lake. The house is smaller than it appears in the photos and not quite as comfortable to just hang out, at least inside.The couch fits three, but there aren't other chairs in the living area. There are great little outside areas though. Communication with Katherine was great. Previous tenants had broken the washer which was a drag and due to weather (drought conditions) we couldn't use...
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
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.

Frequently asked questions

How much do cottages in Woodbury cost?
Prepare to pay between and per night for cottages in Woodbury. No matter your budget, an ideal stay is only clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Woodbury with Expedia?
Reserving a cottage in Woodbury is as simple as deciding on your travel dates and picking your ideal place for outdoor recreation and relaxation. From chic retreats to inexpensive properties and cottages that come with amenities like a kitchenette, Expedia has something for all traveler tastes. As for the best deals around? We’ve got you covered!
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