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

Wassaic Vacation Rentals

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Wassaic vacation rentals

Property grounds

1. Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Dover Plains
10.0 out of 10, Exceptional, (11 reviews)
"We thoroughly enjoyed our stay at this property, clean and spacious tents, impressive shower facility, and all the fun amenities you never thought you needed like an 18 hole putt putt course!"
United States
JoAnna S.
$142 nightly
The price is $160
Sep 7 - Sep 8
Total with taxes and fees
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Smart TV, fireplace, books

2. 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)
"Clean, quiet, well stocked studio with everything we needed for our weekend in Kent. Very convenient to town. Highly recommend!"
United States
Joy P.
$189 nightly
The price is $214
Sep 7 - Sep 8
Total with taxes and fees
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Property grounds

3. Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"The accommodations were wonderful and comfortable."
United States
Chuck S.
$182 nightly
The price is $206
Sep 7 - Sep 8
Total with taxes and fees
Hoppy Hill Farm House
Outdoor dining

4. Glamping, family fun, pet friendly

Glamping, family fun, pet friendly
Dover Plains
10.0 out of 10, Exceptional, (5 reviews)
"Great Glamping spot. The hosts were very responsive and the place provided many activities. "
United States
Gui
$118 nightly
The price is $134
Sep 7 - Sep 8
Total with taxes and fees
Glamping, family fun, pet friendly
Property grounds

5. Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly

Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly
Dover Plains
10.0 out of 10, Exceptional, (5 reviews)
"Fun place with a variety of activities including hot tub, miniature golf, corn bag toss, etc. "
United States
Tania
$127 nightly
The price is $144
Sep 7 - Sep 8
Total with taxes and fees
Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly
Private kitchen

6. 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
$128 nightly
The price is $144
Sep 7 - Sep 8
Total with taxes and fees
Cozy private room in a shared home with a Full-size bed and private bathroom.
Exterior

7. 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)
"We had a wonderful time at this property. It was quaint and clean and right in the middle of town near everything. Thank you, Tanya."
United States
Laurie F.
$434 nightly
The price is $491
Sep 7 - Sep 8
Total with taxes and fees
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Interior

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.
$742 nightly
The price is $839
Sep 10 - Sep 11
Total with taxes and fees
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Terrace/patio

9. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
$609 nightly
The price is $689
Sep 7 - Sep 8
Total with taxes and fees
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Property grounds

10. 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.
$526 nightly
The price is $596
Sep 8 - Sep 9
Total with taxes and fees
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Property grounds

11. 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.
$205 nightly
The price is $223
Sep 8 - Sep 9
Total with taxes and fees
Hudson Valley Farm Getaway- West/Llama Lover Lane
Coffee/tea maker, fridge, oven, stovetop

12. 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.
$184 nightly
The price is $208
Sep 16 - Sep 17
Total with taxes and fees
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Property grounds

13. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (58 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
$233 nightly
The price is $264
Sep 10 - Sep 11
Total with taxes and fees
Mid-Century DJ’s Dream
Smart TV, fireplace

14. 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.
$191 nightly
The price is $216
Sep 15 - Sep 16
Total with taxes and fees
Private, Cozy, Clean apartment in lovely Hyde Park
1 bedroom, desk, WiFi (free), bed sheets

15. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, Exceptional, (32 reviews)
"great place for homebase to visit Hudson Valley area and host was very communicative and helpful"
United States
Brian C.
$280 nightly
The price is $316
Sep 8 - Sep 9
Total with taxes and fees
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
TV, fireplace, books

16. NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
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.
$607 nightly
The price is $685
Sep 22 - Sep 23
Total with taxes and fees
NEW: Chic Modern Barn Style Home in Fun Area
Interior

17. 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, (16 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
$242 nightly
The price is $274
Sep 7 - Sep 8
Total with taxes and fees
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Interior

18. rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
$324 nightly
The price is $363
Sep 8 - Sep 9
Total with taxes and fees
rural, serene + sophisticated space
Dining

19. 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, (9 reviews)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
United States
Polly J.
$984 nightly
The price is $1,113
Sep 7 - Sep 8
Total with taxes and fees
The George is an elegant restored home in the Hudson Valley
Coffee/tea maker, fridge, microwave, oven

20. "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.
$508 nightly
The price is $574
Sep 29 - Sep 30
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms
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.
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Top Wassaic Hotel Reviews

DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

10/10 Excellent
"Check in was smooth and staff was very friendly. The warm chocolate chip cookies were delicious and welcomed. The bed was very comfortable and the shower was relaxing. We were very happy to know the parking garage was included and so convenient being attached to hotel. We loved the proximity to the Walkway Over The Hudson and Alex’s restaurant. We’d definitely stay here again."
Lydia 1-night trip
Posted 4 hours ago
DoubleTree by Hilton Poughkeepsie Convention Center

Find out more about Wassaic

Everything you need to know about Wassaic vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wassaic vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wassaic vacation 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 low season months. For more hustle and bustle, you may prefer to visit Wassaic in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $144 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Wassaic rentals

At Expedia, we put the best Wassaic vacation 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 vacation.

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 vacation rentals in Wassaic?

Yes, we offer vacation rentals close to top local attractions in Wassaic, or you can select a more secluded option if you want a relaxing place to stay.

What's the top vacation rental in Wassaic?

The Chicken Coop: You might want to consider this vacation home rental near Wassaic, which is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 larger area, you’ll find Wing's Castle and Millbrook Vineyards and Winery.

What’s a vacation rental in Wassaic like?

Vacation rentals are private properties you can book for several days or longer in Wassaic. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll have everything you need. If you're concerned about a clean environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a small group gathering.