A misty field with a solitary tree, rolling hills, and a clear sky.

Smallwood Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Smallwood vacation rentals

An outdoor deck with wicker furniture, a fire pit, and a railing.

1. Lakefront Catskills Lodge

Lakefront Catskills Lodge
Monticello
10.0 out of 10, Exceptional, (13 reviews)
"The house is gorgeous, we had a great time!"
United States
Ayden S.
$398 nightly
The price is $447
Nov 3 - Nov 4
Total with taxes and fees
Lakefront Catskills Lodge
A modern outdoor seating area with a sofa and chairs, large glass doors, and a wooden deck.

2. Catskills: Eikonic Box

Catskills: Eikonic Box
Smallwood
10.0 out of 10, Exceptional, (7 reviews)
"Great place to go relax and forget about everything!!!! Definitely must go back "
United States
Jean
$601 nightly
The price is $618
Oct 20 - Oct 21
Total with taxes and fees
Catskills: Eikonic Box
A living room with a wooden floor, a sofa, a dining table with chairs, and a door leading outside.

3. 5 minutes from original Woodstock site.

5 minutes from original Woodstock site.
Mongaup Valley
9.8 out of 10, Exceptional, (76 reviews)
"The house was really nice. Decorated in line with the area. Plus, Bruce was a great host."
United States
Robert
$308 nightly
The price is $347
Oct 18 - Oct 19
Total with taxes and fees
5 minutes from original Woodstock site.
Dining

4. Cozy Cottage w/ Hot Tub! — Family Friendly

Cozy Cottage w/ Hot Tub! — Family Friendly
Mongaup Valley
10.0 out of 10, Exceptional, (10 reviews)
"we had gr8 time with our family even though it rained enjoyed brook fire pit hot tub tramperlin a great place to go with family very freindly host good communication than you alex !!!!"
United States
yisroel k.
$366 nightly
The price is $403
Nov 3 - Nov 4
Total with taxes and fees
Cozy Cottage w/ Hot Tub! — Family Friendly
A dining area with a wooden table and chairs, a hanging light fixture, and a view of the outdoors through large windows.

5. Lakefront Home on Woodstock Way

Lakefront Home on Woodstock Way
White Lake
9.2 out of 10, Wonderful, (12 reviews)
"We had a great time staying at the property. The lake front house and lake access was very nice. Owner/Property manager was great to work with. A great overall experience and would recommend this highly!"
United States
Nolan B.
$389 nightly
The price is $437
Nov 3 - Nov 4
Total with taxes and fees
Lakefront Home on Woodstock Way
Nestled among mature trees, this private escape offers space to relax, reconnect, and unwind

6. Private Riverfront * Family Ready * Wood Stove

Private Riverfront * Family Ready * Wood Stove
Ferndale
10.0 out of 10, Exceptional, (1 review)
"This was an ideal location for our visit to the area. The house and property are beautiful. Really nice kitchen and dining area for cooking, eating, and just visiting. Simple check in and check out directions. We will absolutely consider this property in the future!"
United States
Nancy W.
$641 nightly
The price is $721
Nov 2 - Nov 3
Total with taxes and fees
Private Riverfront * Family Ready * Wood Stove
A circular outdoor seating area with wooden chairs and a central table, surrounded by a stone-paved circle.

7. In the cloud ~your cozy lake house

In the cloud ~your cozy lake house
Swan Lake
9.6 out of 10, Exceptional, (119 reviews)
"We had a wonderful one night stay!"
United States
Anonymous traveler
$310 nightly
The price is $349
Oct 20 - Oct 21
Total with taxes and fees
In the cloud ~your cozy lake house
A modern living room with a sofa, a dining table, and chairs. There is a window with curtains, a lamp, and a painting on the wall.

8. The Resorts World Retreat Spacious 4-bedroom house in beautiful Monticello

The Resorts World Retreat Spacious 4-bedroom house in beautiful Monticello
Monticello
$350 nightly
The price is $394
Oct 17 - Oct 18
Total with taxes and fees
The Resorts World Retreat Spacious 4-bedroom house in beautiful Monticello
A cabin with a wooden deck and a staircase leading to a second-story balcony.

9. Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods

Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods
Narrowsburg
10.0 out of 10, Exceptional, (165 reviews)
"Such a beautiful place to stay and explore with my pup!"
United States
Alison H.
$238 nightly
The price is $268
Oct 19 - Oct 20
Total with taxes and fees
Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods
A house with a dock by a lake, surrounded by trees and a clear sky.

10. Lakeview Cabin Duplex

Lakeview Cabin Duplex
Lake Huntington
9.6 out of 10, Exceptional, (26 reviews)
"Great stay!"
United States
melissa m.
$208 nightly
The price is $234
Oct 20 - Oct 21
Total with taxes and fees
Lakeview Cabin Duplex
A window with a view of a green, leafy outdoor area, possibly a garden or park.

11. Trails Head Tiny House

Trails Head Tiny House
Rock Hill
9.0 out of 10, Wonderful, (21 reviews)
"Host was very friendly and helpful. "
United States
Michael R.
$119 nightly
The price is $133
Nov 1 - Nov 2
Total with taxes and fees
Trails Head Tiny House
A wooden deck with wicker furniture, a red barn, and a forested landscape in the background.

12. Cozy Catskills Farmhouse with Wood-Fired Hot Tub near Bethel Woods

Cozy Catskills Farmhouse with Wood-Fired Hot Tub near Bethel Woods
Cochecton
10.0 out of 10, Exceptional, (9 reviews)
"This is a great property to stay at. Beautiful views and very comfortable accommodations. It is very close to Bethel Woods and had everything 3 Spartan Racers could want."
United States
Scott D.
$430 nightly
The price is $483
Nov 4 - Nov 5
Total with taxes and fees
Cozy Catskills Farmhouse with Wood-Fired Hot Tub near Bethel Woods
A room with a wooden floor, a bed, a TV, and a sign with 'CABIN RULES'.

13. Trails Head Cabin

Trails Head Cabin
Rock Hill
9.8 out of 10, Exceptional, (122 reviews)
"Great location being right at the trailhead for hiking."
United States
Tonne
$196 nightly
The price is $220
Oct 20 - Oct 21
Total with taxes and fees
Trails Head Cabin
A deck with lounge chairs and an umbrella, overlooking a body of water and a building with a blue exterior.

14. Victorian Lake Oasis | Hot Tub | Private Lakefront

Victorian Lake Oasis | Hot Tub | Private Lakefront
Damascus
9.8 out of 10, Exceptional, (10 reviews)
"I was working in the area with two other coworkers and this house was perfect. It had everything we needed and was walking distance to great restaurants. I would definitely stay again if in the area. "
United States
Dave
$390 nightly
The price is $438
Oct 22 - Oct 23
Total with taxes and fees
Victorian Lake Oasis | Hot Tub | Private Lakefront
A tent set up in a forest with a campfire in front.

15. Turey Forest Camping Near Bethel Woods - 15 minutes to Bethel Woods, Casino,

Turey Forest Camping Near Bethel Woods - 15 minutes to Bethel Woods, Casino,
Harris
10.0 out of 10, Exceptional, (1 review)
"Taino wood was a great place for camping. Chantel and her husband Jesse are great host and are very welcoming and kind. Nice place to enjoy with your family in the nature. There were many tent sites inside their woods and we occupied the site called:Turey. We set up 3 tents (two 4-people tents and one 6-people tent). There was a firepit we used to cook food and Chantel and Jesse lend us a pot to cook. Before leaving Chantel, Jesse and a few of their friends sang indigenous songs and played...
United States
Lissette
$94 nightly
The price is $105
Oct 19 - Oct 20
Total with taxes and fees
Turey Forest Camping Near Bethel Woods - 15 minutes to Bethel Woods, Casino,
A residential house with a pathway leading to the front door, surrounded by a well-maintained lawn and trees.

16. New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi

New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi
Hurleyville
10.0 out of 10, Exceptional, (3 reviews)
"Clean, neat, well stocked cabin in a peaceful village. We enjoyed a walk on the nearby rail trail and is not far from other interesting sites. We would definitely recommend."
United States
Holly L.
$202 nightly
The price is $223
Oct 19 - Oct 20
Total with taxes and fees
New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi
An indoor water park with a large water slide, inflatable tubes, and lush greenery.

17. 2 Lake Cabins Pool+hottub Game Room 23acs

2 Lake Cabins Pool+hottub Game Room 23acs
2.0 star property
Highland Lake
$982 nightly
The price is $1,110
Oct 25 - Oct 26
Total with taxes and fees
2 Lake Cabins Pool+hottub Game Room 23acs
A dining area with a wooden table and chairs, a kitchen in the background, and a green wall.

18. Universally Accessible Agrihood Farmhouse Hiking/Fireplace/Getaway

Universally Accessible Agrihood Farmhouse Hiking/Fireplace/Getaway
Hurleyville
10.0 out of 10, Exceptional, (9 reviews)
"Perfect little spot for our weekend visiting Stagedoor! "
United States
Kami E. Q.
$349 nightly
The price is $383
Oct 19 - Oct 20
Total with taxes and fees
Universally Accessible Agrihood Farmhouse Hiking/Fireplace/Getaway
A wooden deck with wicker furniture and a white railing.

19. Cozy 2-bedroom cabin in serene Lake Huntington with AC

Cozy 2-bedroom cabin in serene Lake Huntington with AC
Lake Huntington
10.0 out of 10, Exceptional, (1 review)
"Clean newly renovated cabins where you wake to a beautiful view of the lake and access to boats for the lake. Big deck. Really comfortable."
United States
S C.
$230 nightly
The price is $259
Oct 19 - Oct 20
Total with taxes and fees
Cozy 2-bedroom cabin in serene Lake Huntington with AC
A wooden staircase leading to a garden area with a pathway, rocks, and plants.

20. 3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.
Forestburgh
9.6 out of 10, Exceptional, (16 reviews)
"5 stars across the board! Super communicative host, even offered to change cleaning crew schedule to accommodate our needs. There is a beautiful creek going through the back yard. It’s lovely. I feel like pictures dont do it justice. Definitely a wonderful experience."
United States
Dea
$333 nightly
The price is $374
Oct 20 - Oct 21
Total with taxes and fees
3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.
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 Smallwood Hotel Reviews

Super 8 by Wyndham Monticello NY

Super 8 by Wyndham Monticello NY

10/10 Excellent
"Great job with the redesign. Place looks awesome."
Jonathan 2-night trip
Posted 1 day ago
Super 8 by Wyndham Monticello NY

Find out more about Smallwood

Everything you need to know about Smallwood 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 Smallwood 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 Smallwood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Smallwood vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Smallwood. 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 Smallwood 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 $186 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 Smallwood rentals

At Expedia, we put the best Smallwood 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 Smallwood 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 Smallwood 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 Smallwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Smallwood?

Yes, we give you a choice of vacation rentals close to popular attractions in Smallwood, or you can go with a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals that Smallwood has to offer?

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!: Visitors like this Smallwood vacation home rental. It is located on a lake and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals will I find in Smallwood?

Expedia has 10 vacation rentals for your stay in Smallwood.

What can I see and do in Smallwood?

Forest Reserve at Smallwood and Cliff Lake are a couple of lovely local spots to get outside and enjoy nature. Lake Superior State Park and Bethel Woods Center For The Arts are a couple of places you'll find in the larger area.

What’s a vacation rental in Smallwood like?

Vacation rentals are privately owned properties you can book for a long or short time in Smallwood. Vacation rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a small group gathering.