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

Smallwood Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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.
The price is CA $277
CA $619 total
includes taxes & fees
Nov 5 - Nov 6
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
The price is CA $317
CA $863 total
includes taxes & fees
Nov 3 - Nov 4
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, (77 reviews)
"Great place"
United States
Anonymous traveller
The price is CA $247
CA $453 total
includes taxes & fees
Oct 28 - Oct 29
5 minutes from original Woodstock site.
Exterior

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.
The price is CA $221
CA $571 total
includes taxes & fees
Nov 2 - Nov 3
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.
The price is CA $202
CA $567 total
includes taxes & fees
Oct 29 - Oct 30
Lakefront Home on Woodstock Way
A hallway with a staircase, a door leading outside, and a basket with towels.

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.
The price is CA $200
CA $904 total
includes taxes & fees
Oct 28 - Oct 29
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, (120 reviews)
"We had a wonderful one night stay!"
United States
Anonymous traveller
The price is CA $250
CA $487 total
includes taxes & fees
Oct 28 - Oct 29
In the cloud ~your cozy lake house
A house with a dock by a lake, surrounded by trees and a clear sky.

8. Lakeview Cabin Duplex

Lakeview Cabin Duplex
Lake Huntington
9.6 out of 10, Exceptional, (27 reviews)
"Great stay!"
United States
melissa m.
The price is CA $179
CA $325 total
includes taxes & fees
Oct 28 - Oct 29
Lakeview Cabin Duplex
A room with a sloped ceiling, wooden beams, and two windows with curtains.

9. Trails Head Tiny House

Trails Head Tiny House
Rock Hill
8.8 out of 10, Excellent, (22 reviews)
"Host was very friendly and helpful. "
United States
Michael R.
The price is CA $95
CA $169 total
includes taxes & fees
Oct 28 - Oct 29
Trails Head Tiny House
A room with a wooden floor, a bed, a TV, and a sign with 'CABIN RULES'.

10. Trails Head Cabin

Trails Head Cabin
Rock Hill
9.8 out of 10, Exceptional, (124 reviews)
"Great location being right at the trailhead for hiking."
United States
Tonne
The price is CA $145
CA $273 total
includes taxes & fees
Oct 28 - Oct 29
Trails Head Cabin
A residential house with a pathway leading to the front door, surrounded by a well-maintained lawn and trees.

11. 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.
The price is CA $168
CA $348 total
includes taxes & fees
Oct 28 - Oct 29
New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi
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.
The price is CA $282
CA $668 total
includes taxes & fees
Nov 4 - Nov 5
Cozy Catskills Farmhouse with Wood-Fired Hot Tub near Bethel Woods
A modern outdoor hot tub area with stone walls and a wooden deck.

13. 2 Lake Cabins Pool+hottub Game Room 23acs

2 Lake Cabins Pool+hottub Game Room 23acs
2.0 star property
Highland Lake
The price is CA $222
CA $1,374 total
includes taxes & fees
Nov 3 - Nov 4
2 Lake Cabins Pool+hottub Game Room 23acs
A backyard with a fire pit, outdoor furniture, and a deck.

14. Retro Countryside Cabin | Cozy Upstate NY Private Retreat!

Retro Countryside Cabin | Cozy Upstate NY Private Retreat!
Eldred
9.6 out of 10, Exceptional, (5 reviews)
"The place is exactly as described. Very comfortable and had everything we needed to enjoy our stay. Private and quiet. Bed was very comfortable. Pecks market close by. Will stay again."
United States
Robert R.
The price is CA $107
CA $557 total
includes taxes & fees
Oct 29 - Oct 30
Retro Countryside Cabin | Cozy Upstate NY Private Retreat!
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
The price is CA $94
CA $136 total
includes taxes & fees
Nov 3 - Nov 4
Turey Forest Camping Near Bethel Woods - 15 minutes to Bethel Woods, Casino,
A deck with lounge chairs and an umbrella, overlooking a body of water and a building with a blue exterior.

16. 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
The price is CA $165
CA $609 total
includes taxes & fees
Oct 28 - Oct 29
Victorian Lake Oasis | Hot Tub | Private Lakefront
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.

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

The Resorts World Retreat Spacious 4-bedroom house in beautiful Monticello
Monticello
The price is CA $189
CA $527 total
includes taxes & fees
Oct 28 - Oct 29
The Resorts World Retreat Spacious 4-bedroom house in beautiful Monticello
A stone building with a hot tub, outdoor seating, and a firewood storage area.

18. Lakefront | Sport Courts | HotTub | GameRoom

Lakefront | Sport Courts | HotTub | GameRoom
Highland Lake
10.0 out of 10, Exceptional, (33 reviews)
"We had a wonderful time and definitely would recommend!"
United States
Phillip C.
The price is CA $198
CA $1,229 total
includes taxes & fees
Nov 3 - Nov 4
Lakefront | Sport Courts | HotTub | GameRoom
A dining area with a wooden table and chairs, a kitchen in the background, and a green wall.

19. Universally Accessible Agrihood Farmhouse Hiking/Fireplace/Getaway

Universally Accessible Agrihood Farmhouse Hiking/Fireplace/Getaway
Hurleyville
10.0 out of 10, Exceptional, (11 reviews)
"Perfect little spot for our weekend visiting Stagedoor! "
United States
Kami E. Q.
The price is CA $218
CA $582 total
includes taxes & fees
Oct 28 - Oct 29
Universally Accessible Agrihood Farmhouse Hiking/Fireplace/Getaway
A modern kitchen with grey cabinets, a stainless steel refrigerator, a built-in microwave, and a gas stove.

20. 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, (3 reviews)
"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.
The price is CA $237
CA $391 total
includes taxes & fees
Oct 28 - Oct 29
Cozy 2-bedroom cabin in serene Lake Huntington with AC
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

The Bradstan Boutique Hotel

The Bradstan Boutique Hotel

10/10 Excellent
"I loved our stay here. I would definitely come back."
Sharice 2-night trip
Posted 5 hours ago
The Bradstan Boutique Hotel

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, 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 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Smallwood vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Smallwood vacation rentals we have selected for you start as low as CA $260 per night. Entering your travel dates in the search wizard 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.