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Williamstown Vacation Rentals

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49 rentals in Williamstown.
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Huge Luxe Williamstown Updated Victorian,  All Ensuite Baths, Walk to Spring St!, vacation rental in Williamstown
Huge Luxe Williamstown Updated Victorian,  All Ensuite Baths, Walk to Spring St!, vacation rental in Williamstown
Huge Luxe Williamstown Updated Victorian,  All Ensuite Baths, Walk to Spring St!, vacation rental in Williamstown

Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Charming Downtown Williamstown Cottage - 5 Min Walk to Campus, vacation rental in Williamstown
Charming Downtown Williamstown Cottage - 5 Min Walk to Campus, vacation rental in Williamstown
Charming Downtown Williamstown Cottage - 5 Min Walk to Campus, vacation rental in Williamstown

Charming Downtown Williamstown Cottage - 5 Min Walk to Campus

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Cozy renovated cabin in Williamstown, steps from hiking trails, vacation rental in Williamstown
Cozy renovated cabin in Williamstown, steps from hiking trails, vacation rental in Williamstown
Cozy renovated cabin in Williamstown, steps from hiking trails, vacation rental in Williamstown

Cozy renovated cabin in Williamstown, steps from hiking trails

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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In town 2 bedroom, one bath carriage barn. Sleeps 5., vacation rental in Williamstown
In town 2 bedroom, one bath carriage barn. Sleeps 5., vacation rental in Williamstown
In town 2 bedroom, one bath carriage barn. Sleeps 5., vacation rental in Williamstown

In town 2 bedroom, one bath carriage barn. Sleeps 5.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cozy and quaint country cottage, walk to downtown Williamstown, vacation rental in Williamstown
Cozy and quaint country cottage, walk to downtown Williamstown, vacation rental in Williamstown
Cozy and quaint country cottage, walk to downtown Williamstown, vacation rental in Williamstown

Cozy and quaint country cottage, walk to downtown Williamstown

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Gracious Home with Pool: Private and Spacious,  Close to Town, vacation rental in Williamstown
Gracious Home with Pool: Private and Spacious,  Close to Town, vacation rental in Williamstown
Gracious Home with Pool: Private and Spacious,  Close to Town, vacation rental in Williamstown

Gracious Home with Pool: Private and Spacious, Close to Town

Rental Home
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Tranquil Farmhouse away from the Crowds, vacation rental in Williamstown
Tranquil Farmhouse away from the Crowds, vacation rental in Williamstown
Tranquil Farmhouse away from the Crowds, vacation rental in Williamstown

Tranquil Farmhouse away from the Crowds

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Large, family-friendly farmhouse located in the beautiful Berkshires, vacation rental in Williamstown
Large, family-friendly farmhouse located in the beautiful Berkshires, vacation rental in Williamstown
Large, family-friendly farmhouse located in the beautiful Berkshires, vacation rental in Williamstown

Large, family-friendly farmhouse located in the beautiful Berkshires

Rental Home
7 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Chic Berkshire Dollhouse!, vacation rental in Williamstown
Chic Berkshire Dollhouse!, vacation rental in Williamstown
Chic Berkshire Dollhouse!, vacation rental in Williamstown

Chic Berkshire Dollhouse!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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11 acre mid-century estate, newly renovated, vacation rental in Williamstown
11 acre mid-century estate, newly renovated, vacation rental in Williamstown
11 acre mid-century estate, newly renovated, vacation rental in Williamstown

11 acre mid-century estate, newly renovated

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Private Estate, 5 Bedrooms, Hot Tub, Tranquil Setting!, vacation rental in Williamstown
Private Estate, 5 Bedrooms, Hot Tub, Tranquil Setting!, vacation rental in Williamstown
Private Estate, 5 Bedrooms, Hot Tub, Tranquil Setting!, vacation rental in Williamstown

Private Estate, 5 Bedrooms, Hot Tub, Tranquil Setting!

Rental Home
5 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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family-friendly, private cottage in the beautiful Berkshires, vacation rental in Williamstown
family-friendly, private cottage in the beautiful Berkshires, vacation rental in Williamstown
family-friendly, private cottage in the beautiful Berkshires, vacation rental in Williamstown

family-friendly, private cottage in the beautiful Berkshires

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Thanksgiving week lux condo/4 Berkshires, vacation rental in Williamstown
Thanksgiving week lux condo/4 Berkshires, vacation rental in Williamstown
Thanksgiving week lux condo/4 Berkshires, vacation rental in Williamstown

Thanksgiving week lux condo/4 Berkshires

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Ultra Luxury new home in Williamstown  (3 miles from Williams College, 10 miles, vacation rental in Williamstown
Ultra Luxury new home in Williamstown  (3 miles from Williams College, 10 miles, vacation rental in Williamstown
Ultra Luxury new home in Williamstown  (3 miles from Williams College, 10 miles, vacation rental in Williamstown

Ultra Luxury new home in Williamstown (3 miles from Williams College, 10 miles

Rental Home
7 bedrooms
8 bathrooms
Sleeps 17
Match: Sleeps
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Nestled in the Berkshire Hills, The Manor ensures a joyous experience!, vacation rental in Williamstown
Nestled in the Berkshire Hills, The Manor ensures a joyous experience!, vacation rental in Williamstown
Nestled in the Berkshire Hills, The Manor ensures a joyous experience!, vacation rental in Williamstown

Nestled in the Berkshire Hills, The Manor ensures a joyous experience!

Rental Home
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful Berkshire Lakeside Home In The North Adams/Williamstown Area, vacation rental in Williamstown
Beautiful Berkshire Lakeside Home In The North Adams/Williamstown Area, vacation rental in Williamstown
Beautiful Berkshire Lakeside Home In The North Adams/Williamstown Area, vacation rental in Williamstown

Beautiful Berkshire Lakeside Home In The North Adams/Williamstown Area

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy family friendly home located in the Heart of the Berkshires., vacation rental in Williamstown
Cozy family friendly home located in the Heart of the Berkshires., vacation rental in Williamstown
Cozy family friendly home located in the Heart of the Berkshires., vacation rental in Williamstown

Cozy family friendly home located in the Heart of the Berkshires.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Victorian Home in Bennington, Vermont, vacation rental in Williamstown
Victorian Home in Bennington, Vermont, vacation rental in Williamstown
Victorian Home in Bennington, Vermont, vacation rental in Williamstown

Victorian Home in Bennington, Vermont

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Secluded Luxury In The Country, Close To Culture, vacation rental in Williamstown
Secluded Luxury In The Country, Close To Culture, vacation rental in Williamstown
Secluded Luxury In The Country, Close To Culture, vacation rental in Williamstown

Secluded Luxury In The Country, Close To Culture

Rental Home
4 bedrooms
3 bathrooms
Sleeps 24
Match: Sleeps
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Quarry Hill Farm - stunning views - cozy yet expansive, vacation rental in Williamstown
Quarry Hill Farm - stunning views - cozy yet expansive, vacation rental in Williamstown
Quarry Hill Farm - stunning views - cozy yet expansive, vacation rental in Williamstown

Quarry Hill Farm - stunning views - cozy yet expansive

Rental Home
8 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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Quiet, private setting with panoramic mountain views on our small horse farm., vacation rental in Williamstown
Quiet, private setting with panoramic mountain views on our small horse farm., vacation rental in Williamstown
Quiet, private setting with panoramic mountain views on our small horse farm., vacation rental in Williamstown

Quiet, private setting with panoramic mountain views on our small horse farm.

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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19th c. Renovated Barn in the Berkshires, vacation rental in Williamstown
19th c. Renovated Barn in the Berkshires, vacation rental in Williamstown
19th c. Renovated Barn in the Berkshires, vacation rental in Williamstown

19th c. Renovated Barn in the Berkshires

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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A roomy remodeled retreat close to MassMoCA, vacation rental in Williamstown
A roomy remodeled retreat close to MassMoCA, vacation rental in Williamstown
A roomy remodeled retreat close to MassMoCA, vacation rental in Williamstown

A roomy remodeled retreat close to MassMoCA

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Southern Vermont Farmhouse on 100 Acres, Spectacular Views, Swim Pond, vacation rental in Williamstown
Beautiful Southern Vermont Farmhouse on 100 Acres, Spectacular Views, Swim Pond, vacation rental in Williamstown
Beautiful Southern Vermont Farmhouse on 100 Acres, Spectacular Views, Swim Pond, vacation rental in Williamstown

Beautiful Southern Vermont Farmhouse on 100 Acres, Spectacular Views, Swim Pond

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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New Listing! Berkshires Jiminy Peak Mountainside Condo, vacation rental in Williamstown
New Listing! Berkshires Jiminy Peak Mountainside Condo, vacation rental in Williamstown
New Listing! Berkshires Jiminy Peak Mountainside Condo, vacation rental in Williamstown

New Listing! Berkshires Jiminy Peak Mountainside Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Home in the Berkshires

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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1K sf APT, Harvest to Holiday to Farm Activities, vacation rental in Williamstown
1K sf APT, Harvest to Holiday to Farm Activities, vacation rental in Williamstown
1K sf APT, Harvest to Holiday to Farm Activities, vacation rental in Williamstown

1K sf APT, Harvest to Holiday to Farm Activities

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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COZY, WOODED RETREAT In The Taconic Hills 2+ BR 2.5 BA, large, open LR ., vacation rental in Williamstown
COZY, WOODED RETREAT In The Taconic Hills 2+ BR 2.5 BA, large, open LR ., vacation rental in Williamstown
COZY, WOODED RETREAT In The Taconic Hills 2+ BR 2.5 BA, large, open LR ., vacation rental in Williamstown

COZY, WOODED RETREAT In The Taconic Hills 2+ BR 2.5 BA, large, open LR .

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak., vacation rental in Williamstown
Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak., vacation rental in Williamstown
Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak., vacation rental in Williamstown

Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak.

Rental Home
5 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!, vacation rental in Williamstown
Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!, vacation rental in Williamstown
Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!, vacation rental in Williamstown

Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Two Brooks Lodge - Beautiful Waterfront Vermont Retreat, vacation rental in Williamstown
Two Brooks Lodge - Beautiful Waterfront Vermont Retreat, vacation rental in Williamstown
Two Brooks Lodge - Beautiful Waterfront Vermont Retreat, vacation rental in Williamstown

Two Brooks Lodge - Beautiful Waterfront Vermont Retreat

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Historic c.1880 Victorian MA/VT border near Williams College MassMoCA Freshgrass, vacation rental in Williamstown
Historic c.1880 Victorian MA/VT border near Williams College MassMoCA Freshgrass, vacation rental in Williamstown
Historic c.1880 Victorian MA/VT border near Williams College MassMoCA Freshgrass, vacation rental in Williamstown

Historic c.1880 Victorian MA/VT border near Williams College MassMoCA Freshgrass

Rental Home
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Berkshires Living!! Beautiful Location, Breathtaking Sunset, Fully Renovated Hom, vacation rental in Williamstown
Berkshires Living!! Beautiful Location, Breathtaking Sunset, Fully Renovated Hom, vacation rental in Williamstown
Berkshires Living!! Beautiful Location, Breathtaking Sunset, Fully Renovated Hom, vacation rental in Williamstown

Berkshires Living!! Beautiful Location, Breathtaking Sunset, Fully Renovated Hom

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Whitman Woods - A Berkshire Vacation, vacation rental in Williamstown
Whitman Woods - A Berkshire Vacation, vacation rental in Williamstown
Whitman Woods - A Berkshire Vacation, vacation rental in Williamstown

Whitman Woods - A Berkshire Vacation

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Golden Triangle in the Berkshires, vacation rental in Williamstown
Golden Triangle in the Berkshires, vacation rental in Williamstown
Golden Triangle in the Berkshires, vacation rental in Williamstown

Golden Triangle in the Berkshires

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Christmas in The Berkshires, vacation rental in Williamstown
Christmas in The Berkshires, vacation rental in Williamstown
Christmas in The Berkshires, vacation rental in Williamstown

Christmas in The Berkshires

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Karin's Place, vacation rental in Williamstown
Karin's Place, vacation rental in Williamstown
Karin's Place, vacation rental in Williamstown

Karin's Place

Rental Home
7 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
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The Lodge at Fox Hollow, vacation rental in Williamstown
The Lodge at Fox Hollow, vacation rental in Williamstown
The Lodge at Fox Hollow, vacation rental in Williamstown

The Lodge at Fox Hollow

Rental Home
2 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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The Bear Den, vacation rental in Williamstown
The Bear Den, vacation rental in Williamstown
The Bear Den, vacation rental in Williamstown

The Bear Den

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Wyndham Bentley Brook at ski in/ ski out Jiminy Peak, vacation rental in Williamstown
Wyndham Bentley Brook at ski in/ ski out Jiminy Peak, vacation rental in Williamstown
Wyndham Bentley Brook at ski in/ ski out Jiminy Peak, vacation rental in Williamstown

Wyndham Bentley Brook at ski in/ ski out Jiminy Peak

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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IN/OUT SKIING  CONDO , POOL, MOVIE THEATER/ KIDS ACTIVITIES, vacation rental in Williamstown
IN/OUT SKIING  CONDO , POOL, MOVIE THEATER/ KIDS ACTIVITIES, vacation rental in Williamstown
IN/OUT SKIING  CONDO , POOL, MOVIE THEATER/ KIDS ACTIVITIES, vacation rental in Williamstown

IN/OUT SKIING CONDO , POOL, MOVIE THEATER/ KIDS ACTIVITIES

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Bentley Brook ski in/ski out at Jiminy Peak, vacation rental in Williamstown
Bentley Brook ski in/ski out at Jiminy Peak, vacation rental in Williamstown
Bentley Brook ski in/ski out at Jiminy Peak, vacation rental in Williamstown

Bentley Brook ski in/ski out at Jiminy Peak

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Secluded 19th century Farmhouse with mountain views, vacation rental in Williamstown
Secluded 19th century Farmhouse with mountain views, vacation rental in Williamstown
Secluded 19th century Farmhouse with mountain views, vacation rental in Williamstown

Secluded 19th century Farmhouse with mountain views

Rental Home
8 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
More info
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Luxury Living High Above the Center of Town., vacation rental in Williamstown
Luxury Living High Above the Center of Town., vacation rental in Williamstown
Luxury Living High Above the Center of Town., vacation rental in Williamstown

Luxury Living High Above the Center of Town.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Get Away to the Berkshires: 1 Bedroom Luxury Condo with Outdoor Pool, vacation rental in Williamstown
Get Away to the Berkshires: 1 Bedroom Luxury Condo with Outdoor Pool, vacation rental in Williamstown
Get Away to the Berkshires: 1 Bedroom Luxury Condo with Outdoor Pool, vacation rental in Williamstown

Get Away to the Berkshires: 1 Bedroom Luxury Condo with Outdoor Pool

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Two Brooks Lodge, vacation rental in Williamstown
Two Brooks Lodge, vacation rental in Williamstown
Two Brooks Lodge, vacation rental in Williamstown

Two Brooks Lodge

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Tentrr Signature Site - Hancock Haven, vacation rental in Williamstown
Tentrr Signature Site - Hancock Haven, vacation rental in Williamstown
Tentrr Signature Site - Hancock Haven, vacation rental in Williamstown

Tentrr Signature Site - Hancock Haven

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Art House! Spacious Getaway By Mass Moca, vacation rental in Williamstown
Art House! Spacious Getaway By Mass Moca, vacation rental in Williamstown
Art House! Spacious Getaway By Mass Moca, vacation rental in Williamstown

Art House! Spacious Getaway By Mass Moca

Rental Home
6 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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Enchanting forest hide-away, vacation rental in Williamstown
Enchanting forest hide-away, vacation rental in Williamstown
Enchanting forest hide-away, vacation rental in Williamstown

Enchanting forest hide-away

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Pleasant on Pleasant, vacation rental in Williamstown
Pleasant on Pleasant, vacation rental in Williamstown
Pleasant on Pleasant, vacation rental in Williamstown

Pleasant on Pleasant

Rental Home
2 bedrooms
2 bathrooms
Sleeps 1
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