A large industrial building with a silo-like structure and a smaller attached building.

Wassaic Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Wassaic holiday rentals

A living room with a fireplace, two armchairs, a sofa, and a TV.

1. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (24 reviews)
"Very nice, great location in town"
United States
Lisa F.
The price is AU$354
includes taxes & fees
1 Oct - 2 Oct
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

2. Chic Barn Style * Fireplace * Near Stissing House

Chic Barn Style * Fireplace * Near Stissing House
Pine Plains
10.0 out of 10, Exceptional, (3 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is AU$955
includes taxes & fees
29 Sept - 30 Sept
Chic Barn Style * Fireplace * Near Stissing House
A white house with a steeply pitched roof and a small tower-like structure.

3. Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Millbrook
9.8 out of 10, Exceptional, (6 reviews)
"Lovely home in the heart of Millbrook."
United States
Marianne A S.
The price is AU$685
includes taxes & fees
27 Sept - 28 Sept
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

4. Cozy private room in a shared home with a Full-size bed and private bathroom.

Cozy private room in a shared home with a Full-size bed and private bathroom.
New Milford
10.0 out of 10, Exceptional, (1 review)
"Clean and close to activitys"
United States
randall
The price is AU$230
includes taxes & fees
13 Oct - 14 Oct
Cozy private room in a shared home with a Full-size bed and private bathroom.
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

5. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, Exceptional, (33 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
The price is AU$396
includes taxes & fees
28 Sept - 29 Sept
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A covered outdoor deck with a grill, a chair, and a view of a lake and forest.

6. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is AU$985
includes taxes & fees
1 Oct - 2 Oct
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A deck with a red umbrella, wooden chairs, and a table with potted plants.

7. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (59 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is AU$365
includes taxes & fees
27 Sept - 28 Sept
Mid-Century DJ’s Dream
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

8. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Millbrook
10.0 out of 10, Exceptional, (6 reviews)
"This is a charming, historic, well-maintained home on a beautifully landscaped lot. The updates in the home balance a respect for tradition while also providing modernization. The village of Millbrook is a quintessential twee New England village. The house felt very comfortable and homey and the caretaker was attentive and accommodating. We enjoyed our stay!"
United States
Beth E.
The price is AU$1,163
includes taxes & fees
29 Sept - 30 Sept
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A modern living room with a sectional sofa, a coffee table, and a bar area with stools.

9. Private, Cozy, Clean apartment in lovely Hyde Park

Private, Cozy, Clean apartment in lovely Hyde Park
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"The host was great, the place was really nice and cozy. I would definitely stay here again!!! "
United States
Janet M.
The price is AU$284
includes taxes & fees
28 Sept - 29 Sept
Private, Cozy, Clean apartment in lovely Hyde Park
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

10. Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1

Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1
Hyde Park
8.6 out of 10, Excellent, (4 reviews)
"Great spot if you’re looking for a quiet rural area ! Seeing the llamas made the stay more fun. We weren’t there when the store was open so it was a bit disappointing we couldn’t see more of what the farm offers. We’d definitely go again."
United States
Meg H.
The price is AU$322
includes taxes & fees
27 Sept - 28 Sept
Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1
A modern kitchen with white cabinets, a central island, and a view to the outside.

11. Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.8 out of 10, Exceptional, (7 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is AU$304
includes taxes & fees
12 Oct - 13 Oct
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A rustic cabin surrounded by a forest with a stream in the foreground.

12. Creek Side Cabin with Wood Fired Hot Tub and Fire Pit

Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"Great little house, our favorite part was the gorgeous creek. Absolutely would recommend to pet lovers and those looking for peaceful nature :)"
United States
Kristine W.
The price is AU$675
includes taxes & fees
29 Sept - 30 Sept
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

13. Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Cornwall
10.0 out of 10, Exceptional, (6 reviews)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
The price is AU$735
includes taxes & fees
29 Sept - 30 Sept
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A room with a ceiling fan, a large wall mural, a blue sofa, a colorful rug, and a desk with a chair.

14. THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
Red Hook
9.2 out of 10, Wonderful, (15 reviews)
"Very sweet little spot that took care of all our needs. Very grateful to have found it and enjoyed our stay."
United States
Jason D.
The price is AU$346
includes taxes & fees
7 Oct - 8 Oct
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
A picnic setup with a checkered blanket, a basket, and two wine glasses on a grassy area with a lake and trees in the background.

15. Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
New Fairfield
8.6 out of 10, Excellent, (36 reviews)
"Very serene location, the host was very responsive and helpful."
United States
Stephen L.
The price is AU$495
includes taxes & fees
18 Oct - 19 Oct
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

16. Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
The price is AU$607
includes taxes & fees
28 Sept - 29 Sept
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

17. "Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
Holmes
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is AU$809
includes taxes & fees
7 Oct - 8 Oct
"Country outside the city " 3 bedrooms 2 full bathrooms
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

18. The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.6 out of 10, Exceptional, (10 reviews)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
United States
Polly J.
The price is AU$1,566
includes taxes & fees
26 Sept - 27 Sept
The George is an elegant restored home in the Hudson Valley
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

19. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris
9.8 out of 10, Exceptional, (17 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is AU$395
includes taxes & fees
29 Sept - 30 Sept
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

20. Hudson Valley Farm Getaway- West/Llama Lover Lane

Hudson Valley Farm Getaway- West/Llama Lover Lane
Hyde Park
9.8 out of 10, Exceptional, (8 reviews)
"Great location not too far from the CIA."
United States
alexandra a.
The price is AU$322
includes taxes & fees
27 Sept - 28 Sept
Hudson Valley Farm Getaway- West/Llama Lover Lane
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wassaic Hotel Reviews

The Litchfield Inn

The Litchfield Inn

10/10 Excellent
"This last night of our vacation was the highlight of our stays. From the moment we were greeted upon arrival, to our final farewell, the property exceeded our expectations."
Sharon 1-night trip
Posted 14 hours ago
The Litchfield Inn

Find out more about Wassaic

Everything you need to know about Wassaic holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wassaic holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wassaic holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Wassaic holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wassaic. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wassaic holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wassaic holiday rentals we have selected for you start as low as AU$495 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Wassaic rentals

At Expedia, we put the best Wassaic holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Wassaic rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wassaic holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wassaic. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Wassaic?

Yes, there are holiday rentals close to the most popular sights in Wassaic, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Wassaic has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Wassaic offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Wassaic?

While exploring the area, visit family-friendly sights like White Memorial Conservation Center, or get outside and enjoy nature at Kent Falls State Park. In the wider area, you’ll find Macedonia Brook State Park and Wing's Castle.

What’s a holiday rental in Wassaic like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Wassaic. Holiday rentals offer amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for family trips or small group gatherings.