
Holiday houses in Dutchess County
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Dutchess County
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Dutchess County
Top Guest favourite

Cottage in Clinton Corners
5 out of 5 average rating, 37 reviewsSun Bear Cottage: 3-Bdrm with Sauna
LizRating, 5 stars4 days ago
Very charming home! Host communicated frequently with us. Everything was as described in the listing. Would definitely return in the future.
Guest favourite

Home in Highland
4.89 out of 5 average rating, 47 reviewsHudson Valley Boutique Airb&b
DaniRating, 5 stars5 days ago
It was a great stay and beautiful home. Really appreciated the ease of entry and amazing scenery.
Guest favourite

Bus in Hopewell Junction
5 out of 5 average rating, 8 reviewsBIG RED the Bus at Menlo Pond
NatalyaRating, 5 stars4 weeks ago
great place to relax and very peaceful. fantastic fire pit.
Guest favourite

Guesthouse in Clinton Corners
4.97 out of 5 average rating, 34 reviewsStunning lake side modern barn in Hudson Valley
WillRating, 5 stars1 month ago
Cheryl was a great host and really helped save us when we need overflow space for our retreat.
Guest favourite

Home in Port Ewen
4.93 out of 5 average rating, 27 reviewsHudson Riverfront Mid-Century Modern Home
KevinRating, 5 stars3 weeks ago
A beautiful, comfortable house right on the Hudson with stunning views. We loved watching all the life on the river, herons and loons and ducks, as well as boats from tiny crafts to massive barges. There are great hikes just a short distance away. It is a perfect place to rest, write, draw, and make music.
Guest favourite

Cabin in Carmel Hamlet
4.88 out of 5 average rating, 41 reviewsPeaceful Forest Cabin
ChristopherRating, 5 stars6 days ago
Lanthe and Josephine’s cabin was an absolute dream. From the moment we arrived, we felt completely at peace. The space is warm, thoughtfully decorated, and nestled in such a serene location, perfect for a quiet getaway from the city. Everything was clean, cozy, and exactly as pictured. You can truly feel the love and care that went into creating this space. It was the perfect setting to relax, reconnect, and make meaningful memories. Thank you both for being such gracious and welcoming hosts. We’re already looking forward to returning!
Top Guest favourite

Barn in Hyde Park
4.97 out of 5 average rating, 60 reviewsRed Barn at Turtle Rock Pond
CynthiaRating, 5 stars1 day ago
Max and Emily, we truly loved staying at your barn. Spacious, comfortable and lovely. And you obviously enjoy being hosts, the extras - fresh eggs, snacks, bottled water, and doing all of the cleaning prep (?!)make that obvious! We'd want to stay here if we're in the area again. Thanks again, you're terrific!
Guest favourite

Guest suite in Wingdale
4.98 out of 5 average rating, 43 reviewsDog Tail Corners Studio
MichelleRating, 5 stars2 weeks ago
This wonderful apartment is located just steps away from the Appalachian Trail and nearby dining/shopping in Kent. It was a wonderful place for exploring the area and relaxing in nature. I highly recommend and would happily stay there again.
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- The Kartrite Resort & Indoor Waterpark
- Taconic State Park
- Resorts World Catskills
- Catamount Mountain Ski Resort
- Zoom Flume
- Windham Mountain
- Kent Falls State Park
- Rockland Lake State Park
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Hudson Highlands State Park
- Brotherhood, America's Oldest Winery
- Sterling Forest State Park
- The Stanwich Club
- The Connecticut Golf Club
- Norman Rockwell Museum
- Beartown State Forest
- Mohawk Mountain Ski Area
- Hancock Shaker Village
- Hunter Mountain Resort
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