Smallwood holiday rentals

We found 897 holiday rentals — enter your dates for availability
Discover a selection of 10 homes, 13 cabins and other holiday rentals in Smallwood that are perfect for your trip. Holiday rentals provide the best amenities for your family, friends or furry companion, including parking and a garden. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Smallwood

Showing deals for:25 Dec - 1 Jan

Exterior side photo with extra large patio that includes large outdoor table and seats and barbecues
Dining and front TV room with beautiful outdoor view of the mountains
Interior
Living or TV area at front entrance of cabin
Exceptional
(9 reviews)

The Luxury Cabin at Deep Hollow

Narrowsburg

16% off
AU$10,106
for 7 nights, 1 cabin
AU$1,444 per night
includes taxes & fees
The Luxury Cabin at Deep Hollow
Room
Dining
Interior
Dining
Exceptional
(5 reviews)

Serenity at Lake Joseph | Lakefront•Hot Tub•Ski

Forestburgh

16% off
AU$6,585
for 7 nights, 1 chalet
AU$941 per night
includes taxes & fees
Serenity at Lake Joseph | Lakefront•Hot Tub•Ski
Exterior
Property grounds
Bedroom 1, double bed
View from rear of house, standing at sin-room entryway.
Exceptional
(39 reviews)

Waterfront property, perfect winter getaway, directly on the Willowemoc!

Livingston Manor

11% off
AU$2,309
for 7 nights, 1 cabin
AU$330 per night
includes taxes & fees
Waterfront property, perfect winter getaway, directly on the Willowemoc!
the house
The house
The fields
Dining table
Exceptional
(89 reviews)

The Stone Wall Property on 25 acres with private lake

Hurleyville

8% off
AU$3,535
for 7 nights, 1 cottage
AU$505 per night
includes taxes & fees
The Stone Wall Property on 25 acres with private lake
Exterior
Terrace/patio
Interior
Interior
Exceptional
(27 reviews)

Private log cabin nestled at the base of a secluded wooded area

Yulan

8% off
AU$7,215
for 7 nights, 1 home
AU$1,031 per night
includes taxes & fees
Private log cabin nestled at the base of a secluded wooded area
Pool
Interior
Dining
Indoor spa tub
Exceptional
(43 reviews)

Hemlock Estate: Indoor Hot Tub, Pool, Game Room; Spacious, Ski & More!

Monticello

8% off
AU$8,872
for 7 nights, 1 villa
AU$1,267 per night
includes taxes & fees
Hemlock Estate: Indoor Hot Tub, Pool, Game Room; Spacious, Ski & More!
Peaceful & Quiet Winter Retreat. Enjoy a warm fire and view the iced over lake.
The view as you enter the front door.
The main living area showing living room, dining area and kitchen.
Redesigned safe and well lit staircase and path.
Exceptional
(207 reviews)

Relaxing Lakefront, Very Clean. Great for Families.

Bethel

9% off
AU$4,143
for 7 nights, 1 home
AU$592 per night
includes taxes & fees
Relaxing Lakefront, Very Clean. Great for Families.
Interior
Living area
Exterior
Room
Exceptional
(7 reviews)

lake/fireplace

Greeley

9% off
AU$51,007
for 7 nights, 1 home
AU$7,287 per night
includes taxes & fees
lake/fireplace
Terrace/patio
Private kitchen
Living area
Property grounds
Exceptional
(5 reviews)

Charming 2-bedroom Country Cottage with Hot Tub

Obernburg

12% off
AU$5,440
for 7 nights, 1 cottage
AU$777 per night
includes taxes & fees
Charming 2-bedroom Country Cottage with Hot Tub
Interior
Outdoor dining
Exterior
Living area
Exceptional
(9 reviews)

Immerse in your private woods in our modern cabin

Livingston Manor

11% off
AU$3,986
for 7 nights, 1 cabin
AU$569 per night
includes taxes & fees
Immerse in your private woods in our modern cabin
Kitchen
Hot tub on the deck and open year round
Dining area
Family room with wood stove
Excellent
(13 reviews)

Casa Nera | Heated Pool • Hot Tub • Ski

Swan Lake

16% off
AU$6,585
for 7 nights, 1 home
AU$941 per night
includes taxes & fees
Casa Nera | Heated Pool • Hot Tub • Ski
Exterior
Pool
Dining
Exterior detail
Exceptional
(88 reviews)

Private Hilltop Getaway with Hot Tub & Saltwater Heated Pool

Damascus

8% off
AU$7,162
for 7 nights, 1 home
AU$1,023 per night
includes taxes & fees
Private Hilltop Getaway with Hot Tub & Saltwater Heated Pool
Living area
Terrace/patio
Interior
Exterior
Exceptional
(6 reviews)

Milk House @ Indigo Bunting Farm

Callicoon Center

8% off
AU$4,273
for 7 nights, 1 cottage
AU$610 per night
includes taxes & fees
Milk House @ Indigo Bunting Farm
Property grounds
Private kitchen
Exterior
Private kitchen
Very good
(28 reviews)

Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski

Monticello

8% off
AU$12,026
for 7 nights, 1 home
AU$1,718 per night
includes taxes & fees
Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski
Living area
Dining
Interior
2 Twin Beds
Exceptional
(6 reviews)

Cozy Catskills Farmhouse in Barryville near the Delaware River

Barryville

7% off
AU$2,931
for 7 nights, 1 home
AU$419 per night
includes taxes & fees
Cozy Catskills Farmhouse in Barryville near the Delaware River
Living area
Dining
Outdoor dining
Interior
Exceptional
(7 reviews)

Dancing Doe Estate with Wood Stove, Hot Tub & Firepit

Jeffersonville

12% off
AU$5,577
for 7 nights, 1 home
AU$797 per night
includes taxes & fees
Dancing Doe Estate with Wood Stove, Hot Tub & Firepit
Private kitchen
Exterior
Room
Spacious dining for 6-8 with optional leaf and extra chairs
Exceptional
(11 reviews)

Private 5-Acre Farmhouse Retreat - Bethel Woods 25 mins - Sleeps 8

Livingston Manor

8% off
AU$5,099
for 7 nights, 1 home
AU$728 per night
includes taxes & fees
Private 5-Acre Farmhouse Retreat - Bethel Woods 25 mins - Sleeps 8
Kitchen island
Dining table with 8 chairs
Room
Outdoor fire pit with comfy chairs
Exceptional
(13 reviews)

Private vollyball court: 5-Acre Haven with AC close to Bethel Woods.

Narrowsburg

12% off
AU$5,047
for 7 nights, 1 home
AU$721 per night
includes taxes & fees
Private vollyball court: 5-Acre Haven with AC close to Bethel Woods.
Private kitchen
Pool
Living area
Exterior detail
Exceptional
(7 reviews)

Stylish 2-Bedroom Ski/Lake House in Masthope Mountain Community

Lackawaxen

8% off
AU$2,750
for 7 nights, 1 home
AU$393 per night
includes taxes & fees
Stylish 2-Bedroom Ski/Lake House in Masthope Mountain Community
Marina
Lake front slate patio with fire pit.
Newly renovated living room with a massive pit couch
Living area
Exceptional
(18 reviews)

Enjoy the Magic of the Catskills in your Private Lakefront Home

White Lake

8% off
AU$5,753
for 7 nights, 1 home
AU$822 per night
includes taxes & fees
Enjoy the Magic of the Catskills in your Private Lakefront Home
Room
Exterior
Outdoor dining
Private kitchen
Exceptional
(11 reviews)

Cozy 1-bedroom cabin in amazing Milford with WiFi, AC next to stream.

Milford

8% off
AU$2,218
for 7 nights, 1 cabin
AU$317 per night
includes taxes & fees
Cozy 1-bedroom cabin in amazing Milford with WiFi, AC next to stream.
Private kitchen
Outdoor dining
Interior
Living area
Wonderful
(15 reviews)

Breathtaking River Front Cabin

Damascus

12% off
AU$2,905
for 7 nights, 1 home
AU$415 per night
includes taxes & fees
Breathtaking River Front Cabin
Property grounds
Interior
Living area
Private kitchen
Exceptional
(9 reviews)

Lakefront home w/ Kayaks, canoe & SUP on QUIET & PRIVATE lake NEAR BETHEL WOODS

Monticello

5% off
AU$2,885
for 7 nights, 1 home
AU$412 per night
includes taxes & fees
Lakefront home w/ Kayaks, canoe & SUP on QUIET & PRIVATE lake NEAR BETHEL WOODS
Exterior
Private kitchen
Room
Living area
Wonderful
(10 reviews)

Spacious Port Jervis Home - beautiful views

Port Jervis

8% off
AU$3,620
for 7 nights, 1 home
AU$517 per night
includes taxes & fees
Spacious Port Jervis Home - beautiful views

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    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

Book a holiday rental for your Smallwood getaway

Learn about the unique charm of Smallwood with a stay in a holiday home rental. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Smallwood

Are you searching for things to do while you're in town? Venture out of your holiday home and check out everything that makes Smallwood a fun place to get away to. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Monticello Motor Club (6.6 mi / 10.7 km)
  • Concord Monster Golf Course (8.9 mi / 14.4 km)
  • Sullivan County Golf and Country Club (10.3 mi / 16.5 km)
  • Ski Big Bear at Masthope Mountain (13.8 mi / 22.2 km)
  • Tarry Brae Golf Course (10.4 mi / 16.8 km)
  • Bashakill Vineyards (17.6 mi / 28.3 km)

Exploring the natural features in Smallwood

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Smallwood is a great place to get outside. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Lake Superior State Park (3.3 mi / 5.2 km)
  • Woodstock Monument (4.5 mi / 7.2 km)
  • Mohican Lake (9.3 mi / 15 km)
  • Neversink River (12 mi / 19.3 km)
  • Lake Louise Marie (12.6 mi / 20.2 km)
  • Upper Delaware River (13 mi / 20.9 km)

Frequently asked questions

What is the best area to stay in Smallwood when booking a holiday rental?
When considering a holiday rental in Smallwood, New York, the most appealing area to stay in would be the charming neighbourhood surrounding the Smallwood community itself. This area offers a delightful blend of natural beauty and a serene atmosphere, making it an ideal retreat for those looking to unwind. Visitors can enjoy the picturesque landscapes, with numerous hiking trails and beautiful spots for fishing nearby.One of the top attractions in this vicinity is the Smallwood Forest, which provides ample opportunities for outdoor activities such as hiking and birdwatching, allowing guests to immerse themselves in the local wildlife and stunning scenery. Additionally, the nearby Smallwood Community Centre often hosts various events and activities, providing a sense of community and engagement for those staying in the area.In terms of accommodation options, there are a variety of properties available, from quaint cabins to larger family homes, suiting different preferences and group sizes.
Where are the best areas for renting a beach house in Smallwood?
For renting a beach house in Smallwood, the area around the scenic Smallwood Lake is ideal. This small but picturesque community offers a selection of charming lakeside cabins and houses that provide a serene retreat. Many of these properties come equipped with essential amenities such as outdoor decks, barbecue grills, and fully stocked kitchens, making them great for families or groups looking to enjoy a peaceful getaway by the water.In addition, the nearby Bethel Woods Centre for the Arts offers a variety of cultural events and concerts, ideal for those who appreciate music and arts. Travellers can also enjoy local hiking trails and nature walks in the surrounding areas, with some properties featuring easy access to these outdoor activities.
Where are the best Smallwood ski resort rentals?
For those seeking ski resort rentals near Smallwood, New York, the closest ski areas are located in the nearby Catskill Mountains, particularly within towns like Monticello and Liberty. In Monticello, travellers can find a variety of accommodations, including cosy cabins and family-friendly lodges that often feature amenities such as fully equipped kitchens, fireplaces, and outdoor spaces for relaxation after a day on the slopes.The area around Liberty also offers appealing options with charming chalets and rustic homes that accommodate larger groups or families. Many properties here come with essential features like hot tubs, BBQ grills, and access to nearby hiking trails, making them ideal for both winter sports enthusiasts and those looking to unwind in nature.Additionally, the scenic beauty of the Catskills provides numerous outdoor activities year-round, from skiing in the winter to hiking and fishing in the warmer months. Rentals in this region frequently have convenient access to local dining and shopping, enhancing the overall experience for visitors.
What is the most popular type of holiday rental accomodation in Smallwood?
In Smallwood, cabins are the most popular type of holiday rental, with around 52 available in this charming area. These cabins typically provide a rustic and cosy atmosphere, featuring amenities such as fully equipped kitchens, comfortable living areas, and often outdoor spaces like decks or patios for enjoying the serene surroundings. Additionally, there are about 28 holiday houses and around 20 cottages, which offer similar comforts and are ideal for families or groups seeking more space.
Are there any family house rentals in Smallwood?
In Smallwood, New York, there are several family-friendly house rentals available, with around 14 options to choose from. This charming area is renowned for its serene environment, making it an excellent choice for families looking to escape the hustle and bustle. Many properties in this locale feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces great for children to play and explore.Visitors can also enjoy amenities such as Wi-Fi, comfortable bedrooms, and sometimes even outdoor fire pits for evening gatherings. The natural beauty surrounding Smallwood offers opportunities for hiking and outdoor activities, ideal for family adventures.
Can I rent a holiday home with a pool or hot tub in Smallwood?
In Smallwood, New York, there are several holiday homes available for rent that feature pools and hot tubs. This tranquil area is great for those looking to unwind amidst nature. Many of the properties come equipped with private pools, hot tubs, and spacious outdoor decks, ideal for relaxation after a day of outdoor activities. Inside, travellers can expect amenities such as fully equipped kitchens, comfortable living areas, and sometimes even game rooms for family entertainment.
Are there pet-friendly house rentals in Smallwood?
In Smallwood, there are several pet-friendly house rentals available, with a total of 13 options to choose from. Many of these holiday homes are situated in serene, wooded areas, providing a peaceful retreat for families and their furry friends. Travellers can expect amenities such as fully equipped kitchens, spacious living rooms, and outdoor spaces like decks or patios, superb for enjoying the tranquil surroundings.The neighbourhood is known for its natural beauty, with nearby parks and nature trails that are ideal for walking dogs and exploring the outdoors. Smallwood offers a quaint, rural atmosphere where guests can unwind and reconnect with nature while ensuring their pets are welcome.
Are there any remote work holiday rentals in Smallwood?
In Smallwood, New York, there are numerous options for remote work holiday rentals, with around 80 properties available. This serene area, located in the Catskills, is ideal for those seeking a peaceful environment to work remotely. Many of these rentals come equipped with amenities such as free Wi-Fi, ensuring a reliable internet connection for work tasks.Visitors can expect comfortable accommodations that often feature dedicated workspaces, spacious living areas, and well-equipped kitchens, allowing for a pleasant and productive stay. Additionally, the scenic surroundings provide opportunities for outdoor activities during breaks, making Smallwood a great choice for combining work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Smallwood?
In Smallwood, popular rental amenities include kitchens, which allow guests to prepare their own meals, and decks or patios that provide outdoor space for relaxation and enjoying the natural surroundings. Many rentals also feature fireplaces, great for cosy evenings. Onsite parking is typically available, making it convenient for those travelling by car. Additionally, most accommodations come equipped with coffee and tea makers to enhance the comfort of guests during their stay.
When is the best time to visit Smallwood for a holiday rental?
July is the most popular month to visit Smallwood, New York, drawing in holidaymakers eager to enjoy the charm of this quaint destination. The peak season, spanning from June to August, offers a delightful blend of warm weather and vibrant community events, making it an ideal time for outdoor activities and relaxation. Visitors can relish in the scenic beauty of the surrounding nature, great for hiking, fishing, or simply unwinding by the water.During this season, temperatures typically range from 15 to 30 degrees Celsius, providing a comfortable climate for sightseeing and enjoying various local attractions. Smallwood's serene lakes and lush landscapes create a great backdrop for those looking to immerse themselves in nature and engage in leisurely pursuits.For those who prefer a quieter experience, consider visiting in December. While this is the low season, it offers a unique opportunity to enjoy the serene winter landscape, great for cosy getaways and peaceful retreats. The tranquillity of Smallwood during this month makes it an excellent choice for those looking to recharge away from the hustle and bustle.Ultimately, the best time to book a holiday rental in Smallwood depends on your preference for a lively summer atmosphere or a peaceful winter escape.
What are the top attractions in Smallwood?
In Smallwood, New York, visitors can enjoy a tranquil escape surrounded by nature. The area is renowned for its beautiful lakes, particularly Smallwood Lake, where opportunities for fishing, kayaking, and swimming abound during the warmer months. The picturesque scenery makes it an ideal spot for hiking and exploring the nearby wooded trails.For those interested in local history, the Smallwood Community Church offers a glimpse into the area's past and often hosts community events. The nearby Bethel Woods Centre for the Arts is also a significant attraction, featuring concerts and cultural events throughout the year, and is located just a short drive away, providing a blend of nature and culture.
Are all fees included in the Smallwood holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Smallwood holiday homes with parking?
Stayz offers a wide selection of holiday homes in Smallwood with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Smallwood holiday homes?
You can find great discounts on holiday homes in Smallwood on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Smallwood holiday home booking on Stayz?
To find Smallwood holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Smallwood?
A long-stay holiday home in Smallwood is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Smallwood holiday home?
Book your Smallwood holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Smallwood?
Prices for holiday homes in Smallwood vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Smallwood to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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