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

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, (40)
"Beautiful cottage, spectacular property, wonderful hosts. Not sure what else to say? We came up to CT with our pup to look at areas we may want to move to. The cottage was perfect for us, nice and private and lots of land for our pup to walk. Great state park a few miles away and plenty of good restaurants nearby. Very happy!"
Guest Cottage on Country Estate
Historic Whitneyville Cottage
Exterior detail

Historic Whitneyville Cottage

9.4 out of 10, Exceptional, (13)
"Road noise was annoying. Otherwise as advertised."
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)
"Home was beautifully decorated with a warm cozy feel especially in autumn. Perfect for a family reunion in Litchfield and would highly recommend any time of the year!!"
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
Modern Terryville Cottage w/ Deck & Lake View!
Terryville Vacation Rental | 2BR | 1BA | 800 Sq Ft | 2 Steps to Enter

Modern Terryville Cottage w/ Deck & Lake View!

9.0 out of 10, Wonderful, (4)
"This cottage was just as the pics show. Great communication with host prior to visit as well as a "Thank you" This is the perfect spot to relax & recharge from stress. The cottage wraps you in warmth, and charm."
Modern Terryville Cottage w/ Deck & Lake View!
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, (74)
"The house is as advertised. Good amount of room. The host was pretty communicative. No complaints from the property. Just wish they had a bigger table for group dinners"
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, (15)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
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!
How can I find cheap cottages in Woodbury?
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