The 28 Best Holiday Rentals in Hudson Valley

Ranked 1 out of 300 in the region, as well as being 1 of 5 for holiday rentals in Phoenicia.

• “Amazing location, charming and clean cabin stocked with essentials and the owner was quick to respond to inquiries. Grea”
• “We thoroughly enjoyed our stay in this clean, cozy lodge in a beautiful part of the Catskills!”
• “Clean and cozy, conveniently located”
• See more reviews of Panther Mountain Lodge

Ranked 2 out of 300 in the region, as well as being 1 of 15 for holiday rentals in Kingston.

• “Will be back!”
• “A perfect retreat”
• “Great visit at a great place in a great town”
• See more reviews of The Stables

Ranked 3 out of 300 in the region, as well as being 2 of 4 for holiday rentals in Rhinebeck.

• “Comfortable, thoughtfully designed, responsive hosts, convenient location”
• “Exceptional wee gem.”
• “Great stay for 1 night”
• See more reviews of Private Studio Close to Downtown Rhinebeck

Ranked 4 out of 300 in the region, as well as being 1 of 1 for holiday rentals in Staatsburg.

• “Great value for a quick overnight stay in a private area. Drive carefully at night with all the deer around!”
• “It worked perfect for our brief stay. Worth the price.”
• “I wish we could have stayed longer!”
• See more reviews of Mid-Century DJs Dream near Rhinebeck

Ranked 5 out of 300 in the region, as well as being 1 of 1 for holiday rentals in Stone Ridge.

• “Exceeded expectations. In every way.”
• “Lovely stay at Schoolhouse 11!!”
• “Beautiful property. Excellent stay.”
• See more reviews of Schoolhouse No. 11 * Hudson Valley Upstate Getaway

Ranked 6 out of 300 in the region, as well as being 1 of 1 for holiday rentals in Ulster Park.

• “”
• “Perfect place for a getaway in the Hudson Valley”
• “Very Cozy and relaxing”
• See more reviews of Newly Renovated 3BR Hudson Valley House

Ranked 7 out of 300 in the region, as well as being 1 of 1 for holiday rentals in Woodridge.

• “Cozy cabin getaway”
• “”
• “Great weekend escape”
• See more reviews of Escape to a 3-Bedroom Cabin in Lower Catskills

Ranked 8 out of 300 in the region, as well as being 1 of 8 for holiday rentals in Hunter.

• “that was a terrible, it ruin my trip. the hole plan has to change”
• “”
• “Hosts easily reachable, spacious, clean, affordable.”
• See more reviews of SPECTACULAR CATSKILLS 4 BEDROOM VACATION OASIS- Gorgeous Hunter Mountain Views!

Ranked 9 out of 300 in the region, as well as being 1 of 2 for holiday rentals in Palenville.

• “Location was perfect for the wedding we attended in...”
• “Great place, great hosts - exceeded our expectations.”
• “Perfect”
• See more reviews of Play All Day - Sleep By The Stream at Night - Swimming Hole

Ranked 10 out of 300 in the region, as well as being 1 of 2 for holiday rentals in Prattsville.

• “This place is amazing for a group of friends looking for a sanctuary to relax in! Amazing hosts and amenities!”
• “Three Generation Vacation”
• “Great house for a big group to enjoy the area and relax with family and friends!”
• See more reviews of Prattvilla -Catskill -Mountain Escape 5 BR ,3 bath with Hot tub

Ranked 11 out of 300 in the region, as well as being 2 of 15 for holiday rentals in Kingston.

• “Even on a rainy weekend, everyone had fun.”
• “Cozy and relaxing we loved roasting smores!”
• “An easy and cozy getaway that's not too isolated but gives the feeling of a mini retreat.”
• See more reviews of Campfire Cottage Fireplace, fire pit & no chores!

Ranked 12 out of 300 in the region, as well as being 1 of 1 for holiday rentals in Red Hook.

• “A very welcoming home away from home in a beautiful quiet...”
• “Excellent library!”
• “Beautiful stay in a rural upstate NY setting with wonderful hosts & peaceful surroundings”
• See more reviews of the farmhouse suite at barn & bike

Ranked 13 out of 300 in the region, as well as being 1 of 6 for holiday rentals in Shandaken.

• “Amazing location and views!”
• “”
• “Loved it, this is a place we'd want to come back to.”
• See more reviews of Catskill Cabin, Cool Apartment, 2nd Floor

Ranked 14 out of 300 in the region, as well as being 3 of 12 for holiday rentals in Saugerties.

• “It was,clean and quiet”
• “Great.”
• “Very charming and clean.”
• See more reviews of Country Cottage with beautiful views

Ranked 15 out of 300 in the region, as well as being 4 of 15 for holiday rentals in Poughkeepsie.

• “Accommodation was spotlessly clean with a comfortable bed.”
• “Not recommended.”
• “It’s a lovely historic building.”
• See more reviews of 1 Br Private Victorian Apt in convenient City location on half acre sleeps 4

Ranked 16 out of 300 in the region, as well as being 1 of 9 for holiday rentals in Catskill.

• “”
• “EXCELLENT!!”
• “The staff were great communicators and readily available for...”
• See more reviews of Willow Pond Motel

Ranked 17 out of 300 in the region, as well as being 2 of 3 for holiday rentals in Warwick.

• “We loved this place!”
• “Just perfect”
• “Perfection”
• See more reviews of Cottage at Millpond Falls - A Romantic Escape

Ranked 18 out of 300 in the region, as well as being 1 of 2 for holiday rentals in Cairo.

• “”
• “Great house, great stay!”
• “Amazing”
• See more reviews of Spacious Cozy Getaway ! King Bed, Game Room, Out Door Patio

Ranked 19 out of 300 in the region, as well as being 4 of 15 for holiday rentals in Kingston.

• “”
• “Great apartment with full cooking / entertaining facilities”
• “We’d go back in a heartbeat!”
• See more reviews of The Carriage House Loft

Ranked 20 out of 300 in the region, as well as being 2 of 9 for holiday rentals in Catskill.

• “Great house!”
• “just great .. :-)”
• “Great getaway.”
• See more reviews of Cozy Cottage, Hot Tub, Fire Pit, 15min to Hudson and hiking

Ranked 21 out of 300 in the region, as well as being 1 of 1 for holiday rentals in Rock Hill.

• “Perfect place for a vacation. Very kind owners and we always received all the answers to our questions. Clean, cozy, wi”
• “Everything”
• “The cottage is very well equipped and thoughtful.”
• See more reviews of Catskills Cottage with Lake View Book Now

Ranked 22 out of 300 in the region, as well as being 2 of 10 for holiday rentals in Newburgh.

• “Idyllic home away from home with a view to the Hudson River.”
• “Exceptionally clean and beautifully decorated!”
• “Great stay in the Hudson valley”
• See more reviews of Deck View of Hudson River & Mt Beacon / Boho Suite

Ranked 23 out of 300 in the region, as well as being 6 of 6 for holiday rentals in Woodstock.

• “Pleasurable relaxing”
• “Great house in a sweet location”
• “Great location, close to Tinker St, Opus 40 and kayaking on...”
• See more reviews of Charming Cottage with Yard - 2 Mi to Tinker St!

Ranked 24 out of 300 in the region, as well as being 1 of 1 for holiday rentals in Mountain Dale.

• “Good option for a break from city travelling with good facilities and quiet location.”
• “”
• “We were glad we hadn’t paid more for this place.”
• See more reviews of little cozy house in a village

Ranked 25 out of 300 in the region, as well as being 6 of 15 for holiday rentals in Kingston.

• “Perfect getaway spot for a cozy and quiet retreat.”
• “”
• “It was a perfect place to be comfortable while traveling to see family.”
• See more reviews of Retro Retreat renovated 2BR, desk, no chore list!

Ranked 26 out of 300 in the region, as well as being 4 of 9 for holiday rentals in Catskill.

• “Beautiful house.”
• “Great visit to the Catskills!”
• “Excellent stay. Highly recommended”
• See more reviews of Cabin at Paradise Lake

Ranked 27 out of 300 in the region, as well as being 4 of 4 for holiday rentals in Monroe.

• “”
• “Overall a great place, with only one thing that could’ve been better :)”
• “Location, ease of check-in, accommodating host.”
• See more reviews of Hudson Valley Cottage Rental 3 bedrooms Monroe NY

Ranked 29 out of 300 in the region, as well as being 1 of 2 for holiday rentals in Wurtsboro.

• “Very pleasant - would stay there again”
• “A modern clean cabin on a babbling stream near everything!! Loved it.”
• “Wonderful getaway and the stay at this cabin was perfect.”
• See more reviews of Escape to a Streamside Cabin in the Lower Catskills