Photo by Anna Arsenault

Search Wingdale Cottage Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jul 25 - Jul 27
In two weeks
Aug 1 - Aug 3
In one month
Aug 15 - Aug 17
In two months
Sep 12 - Sep 14

Browse Select Wingdale Cottages

Dainty New Preston Cottage w/ Dock & Lake Views!
Relax by the fire pit surrounded by trees and a serene body of water.

Dainty New Preston Cottage w/ Dock & Lake Views!

9.0 out of 10, Wonderful, (35)
"Loved our time at this cozy cottage by the lake!! Beautiful views and great antique decor in the cottage!!"
Dainty New Preston Cottage w/ Dock & Lake Views!
Two Bedroom Cottage Close To Town
Equipped with a refrigerator, microwave, oven, and dishwasher, this kitchen offers ample space for meal preparation.

Two Bedroom Cottage Close To Town

9.2 out of 10, Wonderful, (22)
"We enjoyed three nights at the cottage. It's beautifully decorated, comfortable, warm and welcoming - a perfect home base for nearby hikes and exploring the area. The large yard was perfect for playing soccer with our child. Renters note: we also had a fabulous meal at nearby restaurant Fern. "
Two Bedroom Cottage Close To Town
Idillic summer getaway in Litchfield Hills, CT.
Surrounded by lush greenery, this house features a gabled roof and a prominent chimney.

Idillic summer getaway in Litchfield Hills, CT.

10.0 out of 10, Exceptional, (13)
"Great spot close to Limerock Raceway - private, cute, and a perfect spot to stay! The owners are so nice and accommodating - I couldn’t say nicer things about this place and will be back!"
Idillic summer getaway in Litchfield Hills, CT.
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!
Relax in a serene outdoor space with a seating area, fire pit, and comfortable chairs.

Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

9.4 out of 10, Exceptional, (91)
"This is a beautiful home even if you live in the area and just want to spend the weekend at the lake, it’s a perfect getaway. We love that it was dog friendly. The host was wonderful and very accommodating. The house came stocked with everything that you would need for a perfect stay. "
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!
Cozy 2-bedroom Cottage with Access to Bantam Lake
Stroll through the lush garden, surrounded by vibrant greenery and colorful flowers, to a serene outdoor space with a wooden fence and inviting bench.

Cozy 2-bedroom Cottage with Access to Bantam Lake

9.6 out of 10, Exceptional, (17)
"Even with horrible weather, we had a wonderful stay!"
Cozy 2-bedroom Cottage with Access to Bantam Lake
Be in Nature at this Gorgeous Riverfront Cabin
Relax in this stylish living room with a sofa, armchair, and coffee table, offering a view of lush greenery.

Be in Nature at this Gorgeous Riverfront Cabin

10.0 out of 10, Exceptional, (18)
"Property was as advertised. Clean and nearby places we wanted to visit while, still being out of the way and quiet."
Be in Nature at this Gorgeous Riverfront Cabin
Pet-friendly Cottage at Historic Millbrook Farm Estate
Traditional dresser with ornate carvings and multiple drawers, featuring a mirror above and a decorative candelabra.

Pet-friendly Cottage at Historic Millbrook Farm Estate

9.0 out of 10, Wonderful, (6)
"Stayed in this renovated farmhouse for a very snowy weekend. Nicely redone and furnished with spacious living/dining area. Could have fit 2 more adults or 2-3 kids. Hosts were lovely and introduced us to the goats. Too snowy and icy to get outdoors or explore much but local village has shops and kitchen was stocked with pantry staples and bottled water, milk/creamers for coffee so arrival day grocery run was not needed. Bonus large picture window let us enjoy the abundant snow from the warmth of...
Pet-friendly Cottage at Historic Millbrook Farm Estate
Reset and Relax in Luxury Cottage
Guests can enjoy a serene forest view from this deck with a sturdy railing.

Reset and Relax in Luxury Cottage

10.0 out of 10, Exceptional, (40)
"Amazing floors, bathroom showers (wow!), and an awesome kitchen."
Reset and Relax in Luxury Cottage
Peaceful Goshen Cottage w/ Screened Porch & Views!
Kitchen features stainless steel appliances, white cabinetry, and a granite countertop.

Peaceful Goshen Cottage w/ Screened Porch & Views!

9.0 out of 10, Wonderful, (31)
"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!
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Kitchen features a microwave, oven, and refrigerator, with ample counter space and a window.

West Cornwall Cabin ~ 4 Mi to Covered Bridge!

3.0 star property
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
Relax in a serene patio setting surrounded by lush greenery and a calm lake view.

Sweet Dotti's Cottage on Candlewood Lake - 60M NYC

9.6 out of 10, Exceptional, (14)
"Perfect location for families with young children and pets to play in the water with limited boat traffic. Great yard with patios and fire pit for relaxing. Property manager was very responsive and great to work with. Would definitely stay again. Thank you for the great vacation memories!"
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
Magnificent Lake View
Property grounds

Magnificent Lake View

2.0 star property
Magnificent Lake View
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Charming single-story house with a gabled roof and inviting front porch.

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

9.4 out of 10, Exceptional, (8)
"The owners freshly love this place"
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Charming 3bdr Magnolia cottage with heated saltwater pool, AC and WiFi in Amenia
Relax by the serene pool surrounded by lush greenery and shaded lounge chairs.

Charming 3bdr Magnolia cottage with heated saltwater pool, AC and WiFi in Amenia

10.0 out of 10, Exceptional, (1)
"This was the perfect size cottage for 5 of us, with two rooms with queen size beds and one small room with a twin. The setting was very pretty, and the salt water heated pool was a good size and my grandchildren enjoyed swimming in it. We were within walking distance of the small town, and I would recommend staying there."
Charming 3bdr Magnolia cottage with heated saltwater pool, AC and WiFi in Amenia
Lakefront Brewster Vacation Rental w/ Private Dock
Relax in this stylish living room with a high ceiling, sofa set, armchairs, and a coffee table, offering a view of the surrounding greenery.

Lakefront Brewster Vacation Rental w/ Private Dock

10.0 out of 10, Exceptional, (7)
"Felt relaxed from first step in the door! Wonderful view, comfortable beds, helpful management, great kitchen! Loved the heated tile floor in main bath! Lots of birds to enjoy with books and binoculars for identifying. "
Lakefront Brewster Vacation Rental w/ Private Dock
Charming, private 2-bedroom cottage on classic New England farm in Washington CT
Two rustic barns stand adjacent to a white picket fence, surrounded by trees and open land.

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

10.0 out of 10, Exceptional, (3)
"Lovely cottage in a beautiful setting. Well appointed and lots of room to relax, both indoor and outdoor. It was a perfect place to stay while we attended a wedding in the area. "
Charming, private 2-bedroom cottage on classic New England farm in Washington CT
Serene Holmes Cottage Near Lakes & Trails!
Fully equipped kitchen with microwave, coffee maker, and gas stove, offering ample storage and a view of the adjacent living area.

Serene Holmes Cottage Near Lakes & Trails!

3.0 star property
Serene Holmes Cottage Near Lakes & Trails!
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
Relax on the lakeside dock with Adirondack chairs and enjoy the tranquil surroundings.

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

10.0 out of 10, Exceptional, (7)
"Loved staying at this spot when dropping our daughter off for school!"
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
Fire Pit + On-site Pond: Hudson Valley Home!
House (4 Bedrooms) | Interior

Fire Pit + On-site Pond: Hudson Valley Home!

3.0 star property
Fire Pit + On-site Pond: Hudson Valley Home!
Pet-friendly Hopewell Junction Home w/ Pool
Enjoy cooking in this well-equipped kitchen with a sink, ample counter space, and a large island for extra workspace.

Pet-friendly Hopewell Junction Home w/ Pool

3.0 star property
10.0 out of 10, Exceptional, (1)
"This house was so incredible. Not only was it in a quiet nice neighborhood the inside was incredible too. Pool table as well as a pool it was perfect for my stay to have fun and enjoy our time. They were very communicative and welcoming to their house. Everything was comfortable and clean. Can’t say any bad things about this place. Definitely going to book again. I already miss it. "
Pet-friendly Hopewell Junction Home w/ Pool
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free