Family-Friendly Vacation Rentals in Ashokan Rail Trail- Woodstock Dike Trailhead, NY: Compare 10+ Sites & Save

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100 Best Family Vacation Rentals in Ashokan Rail Trail- Woodstock Dike Trailhead (Starting from $154)

Charming Cottage with Yard - 2 Mi to Tinker St!
Charming Cottage with Yard - 2 Mi to Tinker St!
House
Woodstock, NY, USA
2.7k from Ashokan Rail Trail- Woodstock Dike Trailhead center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
9.4

Superb

17 reviews

$324
Average price / night
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Beautiful & Spacious Woodstock Home w/ Pool
Beautiful & Spacious Woodstock Home w/ Pool
House
Woodstock, NY, 12498, United States
2.0k from Ashokan Rail Trail- Woodstock Dike Trailhead center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
8.6

Fabulous

12 reviews

$784
Average price / night
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Woodstock Getaway with Hot Tub about 2 Mi to Dtwn!
Woodstock Getaway with Hot Tub about 2 Mi to Dtwn!
House
Woodstock, NY, USA
3.1k from Ashokan Rail Trail- Woodstock Dike Trailhead center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Hot tubs, Places to stay

4 Bedrooms8 Guests
New to Booking
$306
Average price / night
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Charming Cottage w/ Yard - 2 Mi to Tinker St!
Charming Cottage w/ Yard - 2 Mi to Tinker St!
Cottage
Woodstock, NY, 12498-1933, United States
2.7k from Ashokan Rail Trail- Woodstock Dike Trailhead center

AC, Barbecue, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
9.8

Exceptional

29 reviews

$304
Average price / night
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Cozy Woodstock Home with Fire Pit!
Cozy Woodstock Home with Fire Pit!
House
Woodstock, NY, USA
5.2k from Ashokan Rail Trail- Woodstock Dike Trailhead center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
9.3

Superb

4 reviews

$272
Average price / night
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Quaint Woodstock Escape - 2 Mi to Tinker St!
Quaint Woodstock Escape - 2 Mi to Tinker St!
House
Woodstock, NY, 12498, United States
2.7k from Ashokan Rail Trail- Woodstock Dike Trailhead center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Kitchen, Laundry, No Smoking

3 Bedrooms6 Guests
9.6

Exceptional

11 reviews

$415
Average price / night
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Modern Catskills Escape w Open Living Steam Shower Hot Tub w Mountain Views Minutes from Woodstock Trails Suncliff Vista
Modern Catskills Escape w Open Living Steam Shower Hot Tub w Mountain Views Minutes from Woodstock Trails Suncliff Vista
House
Shokan, NY, USA
5.8k from Ashokan Rail Trail- Woodstock Dike Trailhead center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Hot tubs, Places to stay

1 Bedroom6 Guests
9.0

Fabulous

2 reviews

$635
Average price / night
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Charming 4-bedroom house on 2 acres in marvelous Woodstock with WiFi, AC
Charming 4-bedroom house on 2 acres in marvelous Woodstock with WiFi, AC
House
Woodstock, NY, 12401, United States
2.9k from Ashokan Rail Trail- Woodstock Dike Trailhead center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

4 Bedrooms12 Guests
New to Booking
$321
Average price / night
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Retro Retreat renovated 2BR, desk, no chore list!
Retro Retreat renovated 2BR, desk, no chore list!
House
Kingston, NY, USA
7.6k from Ashokan Rail Trail- Woodstock Dike Trailhead center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

2 Bedrooms4 Guests
9.0

Fabulous

18 reviews

$218
Average price / night
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Woodstock Family Home w/ Tree House + Heated Pool
Woodstock Family Home w/ Tree House + Heated Pool
House
Woodstock, NY, 12498, United States
2.9k from Ashokan Rail Trail- Woodstock Dike Trailhead center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Heater, Internet, Kitchen

4 Bedrooms10 Guests
New to Booking
$572
Average price / night
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Esopus Creekside
Esopus Creekside
House
Lake Katrine, NY, USA
7.6k from Ashokan Rail Trail- Woodstock Dike Trailhead center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis, Places to stay

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$422
Average price / night
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Heated Saltwater Pool • 4 Min to Woodstock • Private Deck & Fire Pit
Heated Saltwater Pool • 4 Min to Woodstock • Private Deck & Fire Pit
House
Woodstock, NY, 12498, United States
3.0k from Ashokan Rail Trail- Woodstock Dike Trailhead center

AC, Arcade, Babysitting, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater

4 Bedrooms10 Guests
9.8

Exceptional

36 reviews

$956
Average price / night
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Peaceful Hurley Retreat about 1 Mi to Main Street
Peaceful Hurley Retreat about 1 Mi to Main Street
House
Hurley, NY, USA
7.7k from Ashokan Rail Trail- Woodstock Dike Trailhead center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

3 Bedrooms5 Guests
9.0

Fabulous

2 reviews

$325
Average price / night
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Woodstock Country Guest Suite
Woodstock Country Guest Suite
Apartment
Woodstock, NY, 12498, United States
3.3k from Ashokan Rail Trail- Woodstock Dike Trailhead center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

1 Bedroom2 Guests
9.8

Exceptional

7 reviews

$154
Average price / night
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Saugerties Farmhouse Sauna and Countryside Views
Saugerties Farmhouse Sauna and Countryside Views
House
Saugerties, NY, USA
8.4k from Ashokan Rail Trail- Woodstock Dike Trailhead center

Cheap, Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
8.4

Very Good

5 reviews

$294
Average price / night
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Catskill Spring Adventures! Book this cottage w/ hot tub & indoor fireplace
Catskill Spring Adventures! Book this cottage w/ hot tub & indoor fireplace
Cottage
Hurley, NY, 12443, United States
3.3k from Ashokan Rail Trail- Woodstock Dike Trailhead center

AC, Barbecue, Crib, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

1 Bedroom4 Guests
10.0

Exceptional

198 reviews

$420
Average price / night
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Campfire Cottage Fireplace, fire pit & no chores!
Campfire Cottage Fireplace, fire pit & no chores!
House
Kingston, NY, USA
9.0k from Ashokan Rail Trail- Woodstock Dike Trailhead center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
9.7

Exceptional

18 reviews

$185
Average price / night
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Fall Foliage Getaway!
Fall Foliage Getaway!
House
Woodstock, NY, 12498, United States
3.7k from Ashokan Rail Trail- Woodstock Dike Trailhead center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms7 Guests
10.0

Exceptional

12 reviews

$733
Average price / night
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Retro Retreat: 1br home w/WFH desk, livingroom, and fire pit
Retro Retreat: 1br home w/WFH desk, livingroom, and fire pit
House
Kingston, NY, USA
9.0k from Ashokan Rail Trail- Woodstock Dike Trailhead center

Pet Friendly, Parking, Guest Services, Security/Safety, Air Conditioner, Internet, Child Friendly

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$300
Average price / night
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New Luxury 5BR3BTh Woodstock Secret Retreat Near all Ski MT Heated Pool& Hot Tub
New Luxury 5BR3BTh Woodstock Secret Retreat Near all Ski MT Heated Pool& Hot Tub
Villa
Woodstock, NY, 12498, United States
3.9k from Ashokan Rail Trail- Woodstock Dike Trailhead center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking

5 Bedrooms11 Guests
9.6

Exceptional

28 reviews

$871
Average price / night
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 Woodstock Cottage with hot tub. Close to town yet very private.
Woodstock Cottage with hot tub. Close to town yet very private.
Cottage
Woodstock, NY, 12433, United States
4.1k from Ashokan Rail Trail- Woodstock Dike Trailhead center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
9.4

Superb

90 reviews

$434
Average price / night
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Maison Noir: Upstate Oasis | Chic Design | Pool + Hot Tub
Maison Noir: Upstate Oasis | Chic Design | Pool + Hot Tub
House
Woodstock, NY, 12498, United States
4.2k from Ashokan Rail Trail- Woodstock Dike Trailhead center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms6 Guests
New to Booking
$527
Average price / night
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Woodstock Mountaintop Country Compound w. Pool & Sauna on 10 Acres
Woodstock Mountaintop Country Compound w. Pool & Sauna on 10 Acres
House
Woodstock, NY, 12498, United States
4.2k from Ashokan Rail Trail- Woodstock Dike Trailhead center

AC, Balcony, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms10 Guests
New to Booking
$342
Average price / night
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LARGE COZY HOME Pool/Pond! 5 Br., 4 Baths. Sleeps 11, Pvt. Quiet, Grill, Firepit
LARGE COZY HOME Pool/Pond! 5 Br., 4 Baths. Sleeps 11, Pvt. Quiet, Grill, Firepit
House
Kingston, NY, 12401, United States
4.2k from Ashokan Rail Trail- Woodstock Dike Trailhead center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

5 Bedrooms11 Guests
10.0

Exceptional

63 reviews

$582
Average price / night
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NEW!  Woodstock-Private-Exquisite-Modern A-Frame-Minimum Stays are Monthly!
NEW! Woodstock-Private-Exquisite-Modern A-Frame-Minimum Stays are Monthly!
House
Woodstock, NY, 12498, United States
4.3k from Ashokan Rail Trail- Woodstock Dike Trailhead center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms15 Guests
10.0

Exceptional

2 reviews

$362
Average price / night
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Serene Woodstock 3 bedroom cottage with sweeping mountain views
Serene Woodstock 3 bedroom cottage with sweeping mountain views
House
Woodstock, NY, 12498, United States
4.4k from Ashokan Rail Trail- Woodstock Dike Trailhead center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms5 Guests
10.0

Exceptional

18 reviews

$397
Average price / night
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Exquisite Chalet by Ashokan water & Woodstock’s most scenic sites-WITH GENERATOR
Exquisite Chalet by Ashokan water & Woodstock’s most scenic sites-WITH GENERATOR
Ski Chalet
Hurley, NY, 12443, United States
4.7k from Ashokan Rail Trail- Woodstock Dike Trailhead center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

3 Bedrooms6 Guests
10.0

Exceptional

158 reviews

$310
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Vacation Rentals in Ashokan Rail Trail- Woodstock Dike Trailhead.

Ashokan Rail Trail- Woodstock Dike Trailhead Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 100 verified family-friendly vacation rentals in Ashokan Rail Trail- Woodstock Dike Trailhead. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Ashokan Rail Trail- Woodstock Dike Trailhead vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $154 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Ashokan Rail Trail- Woodstock Dike Trailhead offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Ashokan Rail Trail- Woodstock Dike Trailhead are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Ashokan Rail Trail- Woodstock Dike Trailhead often include amenities such as Child Friendly, Fireplace/Heating, and Internet. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.