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Bearsville Holiday Rentals

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50 rentals in Bearsville.
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Updated/Pet-Friendly Cabin By Hikes and Woodstock!, holiday rental in Bearsville

Updated/Pet-Friendly Cabin By Hikes and Woodstock!

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Tentrr Signature Site - Shady Knolls, holiday rental in Bearsville

Tentrr Signature Site - Shady Knolls

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!, holiday rental in Bearsville

Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Streamside Cottage Walking Distance to Town of Woodstock, holiday rental in Bearsville

Streamside Cottage Walking Distance to Town of Woodstock

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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SECLUDED POOL, SPA & STREAM on 7 Acres, JUST 5 MINUTES FROM TOWN, holiday rental in Bearsville

SECLUDED POOL, SPA & STREAM on 7 Acres, JUST 5 MINUTES FROM TOWN

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded Catskill Mountain Log Cabin, Breathtaking Vista, Private, Relaxing, holiday rental in Bearsville

Secluded Catskill Mountain Log Cabin, Breathtaking Vista, Private, Relaxing

4 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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Charming Artist's Cottage, holiday rental in Bearsville

Charming Artist's Cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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SPRING at CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi, holiday rental in Bearsville

SPRING at CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Hilltop Treehouse Woodstock Retreat, holiday rental in Bearsville

Hilltop Treehouse Woodstock Retreat

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Romantic Country Barn By the Stream, holiday rental in Bearsville

Romantic Country Barn By the Stream

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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COUNTRY HOME Fenced Backyard, 1 mi. to Town, Kids & Dogs OK!, holiday rental in Bearsville

COUNTRY HOME Fenced Backyard, 1 mi. to Town, Kids & Dogs OK!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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House on 35 Acres w/Mt Views, Private Trails & Creeks, holiday rental in Bearsville

House on 35 Acres w/Mt Views, Private Trails & Creeks

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Country Cabin in Woodstock, NY- Cozy and Pet Friendly, holiday rental in Bearsville

Country Cabin in Woodstock, NY- Cozy and Pet Friendly

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Margaret's Cottage New listing Woodstock Village, holiday rental in Bearsville

Margaret's Cottage New listing Woodstock Village

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace, holiday rental in Bearsville

HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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with mountain views, minutes from Woodstock, NY, holiday rental in Bearsville

with mountain views, minutes from Woodstock, NY

4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Modern Glass House, Minutes to Town, holiday rental in Bearsville

Modern Glass House, Minutes to Town

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious, Private, Close to Town, Work From Home, holiday rental in Bearsville

Spacious, Private, Close to Town, Work From Home

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Pet Friendly Cabin Doh-Ray Up At 1450ft, holiday rental in Bearsville

Pet Friendly Cabin Doh-Ray Up At 1450ft

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Contemporary, Secluded Cabin In The Heart of Woodstock, holiday rental in Bearsville

Contemporary, Secluded Cabin In The Heart of Woodstock

1 bedroom
1 bathroom
Sleeps 4
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Privacy & Luxury @  Heart of Woodstock w/ Hot Tub, holiday rental in Bearsville

Privacy & Luxury @ Heart of Woodstock w/ Hot Tub

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Hot Tub & Heated Pool in Prime Woodstock Gut Renovated Modern Home, holiday rental in Bearsville

New Hot Tub & Heated Pool in Prime Woodstock Gut Renovated Modern Home

5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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LIVE IN NATURE - WALK TO TOWN- CHILDREN LOVE US- SIT BY THE CAMP FIRE, holiday rental in Bearsville

LIVE IN NATURE - WALK TO TOWN- CHILDREN LOVE US- SIT BY THE CAMP FIRE

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Gorgeous Villa w/ Mountain Views, pool, hot tub!, holiday rental in Bearsville

Gorgeous Villa w/ Mountain Views, pool, hot tub!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Mid Century Ranch-Hot Tub-Minutes to Center ofTown, holiday rental in Bearsville

Mid Century Ranch-Hot Tub-Minutes to Center ofTown

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Marigold cabin by the stream -  Heart of Woodstock with Hot Tub & Fireplace, holiday rental in Bearsville

Marigold cabin by the stream - Heart of Woodstock with Hot Tub & Fireplace

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Woodstock Retreat Vacation Home, holiday rental in Bearsville

Woodstock Retreat Vacation Home

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Margaret's Cottage in Woodstock Village, holiday rental in Bearsville

Margaret's Cottage in Woodstock Village

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Woodstock Mediterranean Retreat, holiday rental in Bearsville

Woodstock Mediterranean Retreat

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Tannery Brook Cottage: Terraced Garden with Patio, Cascade and Fire Pit., holiday rental in Bearsville

Tannery Brook Cottage: Terraced Garden with Patio, Cascade and Fire Pit.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxe Bohemian Cabin, Secluded, 6 min to Woodstock, holiday rental in Bearsville

Luxe Bohemian Cabin, Secluded, 6 min to Woodstock

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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charming woodstock cottage with outdoor hottub, holiday rental in Bearsville

charming woodstock cottage with outdoor hottub

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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BLUEBERRY HILL CABIN, holiday rental in Bearsville

BLUEBERRY HILL CABIN

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Woodstock Stone Cottage Swim Lake 3 ski resorts fishing hiking biking music arts, holiday rental in Bearsville

Woodstock Stone Cottage Swim Lake 3 ski resorts fishing hiking biking music arts

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Teahouse Cottage, holiday rental in Bearsville

Teahouse Cottage

50 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tranquil Woodstock Home in the Woods with Hot Tub and Ping Pong, holiday rental in Bearsville

Tranquil Woodstock Home in the Woods with Hot Tub and Ping Pong

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stay and Play! Walk to Town, Onsite Restaurant, Golf Included., holiday rental in Bearsville

Stay and Play! Walk to Town, Onsite Restaurant, Golf Included.

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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2 BR Cabin, Hot Tub, Fireplace, Heart of Woodstock, holiday rental in Bearsville

2 BR Cabin, Hot Tub, Fireplace, Heart of Woodstock

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming Converted Barn On 2+ Acres  Walk To Town, holiday rental in Bearsville

Charming Converted Barn On 2+ Acres Walk To Town

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Tranquil Retreat Stunning Views+Hot Tub, Woodstock Area-Glenford House, holiday rental in Bearsville

Tranquil Retreat Stunning Views+Hot Tub, Woodstock Area-Glenford House

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Woodstock Carriage House, holiday rental in Bearsville

Woodstock Carriage House

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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'Casa Reál' ~ Expansive Woodstock House w/Hot Tub!, holiday rental in Bearsville

'Casa Reál' ~ Expansive Woodstock House w/Hot Tub!

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Celebrate Woodstock & the Surrounding Area, Walk To Town, Swimming Pond., holiday rental in Bearsville

Celebrate Woodstock & the Surrounding Area, Walk To Town, Swimming Pond.

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Glamping at Woodstock Meadows - Outdoor B&B (2 secluded tents w/amenities), holiday rental in Bearsville

Glamping at Woodstock Meadows - Outdoor B&B (2 secluded tents w/amenities)

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Family-Friendly Home: 5 Mins to Central Woodstock, holiday rental in Bearsville

Family-Friendly Home: 5 Mins to Central Woodstock

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Cranberry House in the Catskills, holiday rental in Bearsville

The Cranberry House in the Catskills

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Yankeetown Pond Peace of Mind, holiday rental in Bearsville

Tentrr Signature Site - Yankeetown Pond Peace of Mind

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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Woodstock Sanctuary Spa Retreat - walk to town!, holiday rental in Bearsville

Woodstock Sanctuary Spa Retreat - walk to town!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Charming Cottage w/ Yard - 2 Mi to Tinker St!, holiday rental in Bearsville

NEW! Charming Cottage w/ Yard - 2 Mi to Tinker St!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Sioux Tipi on the waterfall, holiday rental in Bearsville

Sioux Tipi on the waterfall

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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