Holiday houses in Castleton-on-Hudson

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Top-rated holiday rentals in Castleton-on-Hudson

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Cottage in Kinderhook

4.98 out of 5 average rating, 171 reviews

The Cottage on Sylvester Street

The Cottage on Sylvester Street welcomes guests looking for a relaxing weekend or longer stay in a small-village setting. Located at the heart of the historic Village of Kinderhook, this stylishly renovated house is located amongst Kinderhook's collection of historic architectural gems. Within easy walking distance are eateries, wine and beer bars, The School I Jack Shainman Gallery, historic sites, the farmers' market plus farm stands, and quiet, scenic roads perfect for walking and cycling.

18–25 Sep

$256 NZD per night

Guest favourite

Cottage in Valatie

4.99 out of 5 average rating, 127 reviews

Kinderhook Lake Retreat-private+kayaks/sup+swim+ac

Welcome to our paradise-where time slows down and memories are made. It's the perfect retreat for relaxing, kayaking, swimming, hiking, biking, and so much more. -Sip your coffee on the decks while enjoying wildlife -Grab a kayak or paddleboard and explore the lake -Catch the sunset, then take a scenic walk on the Electric Trail -End the day sharing stories around the starlit firepit Close to restaurants, breweries, wineries, galleries, historical sites, trails, farm stores, and orchards.

24 Sep – 1 Oct

$678 NZD per night

Guest favourite

Guest suite in Albany

4.92 out of 5 average rating, 217 reviews

Garden Apartment in Historic Center Square Home

Welcome to our charming studio in the heart of Albany's Center Square. Nestled in one of the oldest homes in the neighborhood, the space has been restored to blend history with modern convenience. Recently renovated, it features a modern bathroom with rain shower. The décor is a nod to mid-century aesthetics. This cozy studio is a stone's throw away from Albany's main attractions within easy walking distance. Experience a unique blend of past and present in this delightful Albany retreat.

11–18 Jun

$140 NZD per night

Guest favourite

Farm stay in Nassau

4.98 out of 5 average rating, 59 reviews

Private 1830 farm house perfect for a country stay

We welcome you to come stay in our private 1830s original saltbox family farm house. Two beautifully redone bedrooms, a remodeled kitchen and bathroom make this the perfect house for a relaxing getaway. Enjoy the gorgeous private 64 acre countryside from the screened in porch or venture out to explore our 1.5 mile mowed hiking trail through the fields, forest, past the rock quarry, wetlands, and fishing pond. Located about 10 miles from Albany and Columbia County is just down the road.

17–24 May

$253 NZD per night

Guest favourite

Apartment in Glenmont

4.94 out of 5 average rating, 33 reviews

Detached Studio Apartment

Private Studio Apartment within our detached Garage. Situated just 3 miles from downtown Albany but far enough to be a private country setting setback in the woods. We live on-site in the house nearby with a shared gravel driveway should you need anything during your stay. Setup similar to a hotel room with queen bed, bathroom and kitchen including sink, mini fridge, dishwasher, cabinets, and counter space. Pet & Kid friendly with a PackNPlay or air mattress upon request. Strong internet.

17–24 May

$219 NZD per night

Guest favourite

Home in Albany

4.99 out of 5 average rating, 208 reviews

Our Antique Bungalow

Enjoy the private and clean comfort of our freshly renovated bungalow in Albany's quaint Helderberg Neighborhood. Some of the regions most cherished restaurants on New Scotland Avenue are within a two block walk. Close accessibility to both Albany Med Hospital and Saint Peters Hospital as well as Albany Law, The Albany School of Pharmacy and Russell Sage College. This home features a newly renovated fully functioning kitchen, a luxurious bathroom with a walk-in shower and full size tub.

1–8 Jan

$321 NZD per night

Guest favourite

Apartment in Albany

4.99 out of 5 average rating, 150 reviews

Beautiful Center Square Garden-Level Unit

This completely modernized garden-level space provides a charming and unique atmosphere while also being centrally located in the Capital Region of New York. My partner and I have taken ample time to carefully craft this space to maximize its potential and ensure your enjoyment. Featuring a fully loaded kitchen with stainless steal appliances, marble countertops, exposed brick throughout, tasteful decor, and your own private patio. We truly hope you enjoy this space as much as we do!

10–17 Oct

$203 NZD per night

Guest favourite

Guest suite in Valatie

4.98 out of 5 average rating, 230 reviews

Guest Suite in Old Chatham Hunt Country

Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!

27 Sep – 4 Oct

$166 NZD per night

Guest favourite

Home in Chatham

4.9 out of 5 average rating, 144 reviews

2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV

WELCOME ALL. Pedestrian/Bike friendly Village home sits 200' to fine dining & Main St pubs/pizza/movies/shopping. 12mi Hudson Amtrak (taxi, Uber avail). Walk to town park w/swim pond. 30mins Albany/Lenox. Keyless entry. Hosts a text away if needed. Smoke/Pet-free property. Check-in 4pm/-out 11a. 55" Sony Roku TV. Reliable high-speed WiFi. Stocked kitchen/full bath incl W/D. Private outdoor dining area w/propane bbq. 2 guests max preferred, a 3rd could be accommodated at extra charge.

21–28 Mar

$213 NZD per night

Guest favourite

Apartment in Delmar

4.99 out of 5 average rating, 171 reviews

Spacious Apartment at the Back of the Tudor House

Enjoy your privacy in this completely renovated, modern two bedroom apartment with full bathroom, and fully equipped kitchen at the rear of the 120 year old English Tudor house, with a private entrance, and self check-in. Located in the heart of Delmar, within walking distance to restaurants, and bars, 0.3 mile to Stram Center for Integrative Medicine, about eight minutes drive to Downtown Albany, seven minutes of the Interstate 87 exit, and twenty minutes from the Albany airport.

15–22 Aug

$331 NZD per night

Guest favourite

Earthen home in West Sand Lake

4.98 out of 5 average rating, 150 reviews

The Hobbit House at June Farms

Enjoy 120-acres of beautiful farmland while you stay in your very own Hobbit house! Nestled in the hills of Hudson Valley, June Farms is a gorgeous animal sanctuary. During your stay, you will be able to meet our Shire horses, Scottish highland cows, Gloucestershire spotted pigs, Nigerian dwarf goats, many chickens and ducks! From June 1 - Labor Day, the bar & restaurant is open most days for you to enjoy (check our calendar to be sure). We look forward to meeting you!

6–13 Mar

$623 NZD per night

Guest favourite

Farm stay in Coeymans Hollow

4.85 out of 5 average rating, 576 reviews

Magic Forest Farm's Mountain View Suite

Our 225 acre farm is predominantly forested, with miles of hiking trails and incredible views. Nestled in the foothills of the Catskills near Albany, we are the last home on a dead end road and have multiple secluded rentals. We are a homestead devoted to the principles of organic farming and self reliance. We grow much of our own food and forge many types of wild mushrooms. You will be sure to enjoy friendly animals around the farm and a private fenced Koi pond.

13–20 Jun

$178 NZD per night