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Old Chatham Holiday Apartments

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51 rentals in Old Chatham.
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Spectacular All Seasons Retreat with Amazing Views, holiday rental in Old Chatham
Spectacular All Seasons Retreat with Amazing Views, holiday rental in Old Chatham
Spectacular All Seasons Retreat with Amazing Views, holiday rental in Old Chatham

Spectacular All Seasons Retreat with Amazing Views

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 14
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Pond View Cottage in Old Chatham WEEKLY & MONTHLY DISCOUNTS OFFERED!!!!, holiday rental in Old Chatham
Pond View Cottage in Old Chatham WEEKLY & MONTHLY DISCOUNTS OFFERED!!!!, holiday rental in Old Chatham
Pond View Cottage in Old Chatham WEEKLY & MONTHLY DISCOUNTS OFFERED!!!!, holiday rental in Old Chatham

Pond View Cottage in Old Chatham WEEKLY & MONTHLY DISCOUNTS OFFERED!!!!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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Beautifully Renovated Exposed Beam Bungalow, holiday rental in Old Chatham
Beautifully Renovated Exposed Beam Bungalow, holiday rental in Old Chatham
Beautifully Renovated Exposed Beam Bungalow, holiday rental in Old Chatham

Beautifully Renovated Exposed Beam Bungalow

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming Farm House on 460 Acre Working Farm, holiday rental in Old Chatham
Charming Farm House on 460 Acre Working Farm, holiday rental in Old Chatham
Charming Farm House on 460 Acre Working Farm, holiday rental in Old Chatham

Charming Farm House on 460 Acre Working Farm

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hudson Old Chatham Loft, holiday rental in Old Chatham
Hudson Old Chatham Loft, holiday rental in Old Chatham
Hudson Old Chatham Loft, holiday rental in Old Chatham

Hudson Old Chatham Loft

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Secluded House with Picturesque Views in Historic Old Chatham, NY, holiday rental in Old Chatham
Secluded House with Picturesque Views in Historic Old Chatham, NY, holiday rental in Old Chatham
Secluded House with Picturesque Views in Historic Old Chatham, NY, holiday rental in Old Chatham

Secluded House with Picturesque Views in Historic Old Chatham, NY

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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The Hudson 2 bedroom bungalow apartment at the Wilbur Estate, holiday rental in Old Chatham
The Hudson 2 bedroom bungalow apartment at the Wilbur Estate, holiday rental in Old Chatham
The Hudson 2 bedroom bungalow apartment at the Wilbur Estate, holiday rental in Old Chatham

The Hudson 2 bedroom bungalow apartment at the Wilbur Estate

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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nesteldown pet friendly, holiday rental in Old Chatham
nesteldown pet friendly, holiday rental in Old Chatham
nesteldown pet friendly, holiday rental in Old Chatham

nesteldown pet friendly

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spend September at this Spectacular and Private Columbia County Estate, holiday rental in Old Chatham
Spend September at this Spectacular and Private Columbia County Estate, holiday rental in Old Chatham
Spend September at this Spectacular and Private Columbia County Estate, holiday rental in Old Chatham

Spend September at this Spectacular and Private Columbia County Estate

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful 6+ Bedroom Farmhouse On 460 Acre Working Farm, holiday rental in Old Chatham
Beautiful 6+ Bedroom Farmhouse On 460 Acre Working Farm, holiday rental in Old Chatham
Beautiful 6+ Bedroom Farmhouse On 460 Acre Working Farm, holiday rental in Old Chatham

Beautiful 6+ Bedroom Farmhouse On 460 Acre Working Farm

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Heaven Cant Wait, On Beautiful Kinderhook, holiday rental in Old Chatham
Heaven Cant Wait, On Beautiful Kinderhook, holiday rental in Old Chatham
Heaven Cant Wait, On Beautiful Kinderhook, holiday rental in Old Chatham

Heaven Cant Wait, On Beautiful Kinderhook

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Berkshire Country Estate: Enjoy beautiful 60 acre estate for a special vacation!, holiday rental in Old Chatham
Berkshire Country Estate: Enjoy beautiful 60 acre estate for a special vacation!, holiday rental in Old Chatham
Berkshire Country Estate: Enjoy beautiful 60 acre estate for a special vacation!, holiday rental in Old Chatham

Berkshire Country Estate: Enjoy beautiful 60 acre estate for a special vacation!

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 16
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Heavenly Kinderhook Lake!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Close to Skiing Heated Pool /Hot Tub/20 acres/Fiber Optic/Chef by Arrangement, holiday rental in Old Chatham
Close to Skiing Heated Pool /Hot Tub/20 acres/Fiber Optic/Chef by Arrangement, holiday rental in Old Chatham
Close to Skiing Heated Pool /Hot Tub/20 acres/Fiber Optic/Chef by Arrangement, holiday rental in Old Chatham

Close to Skiing Heated Pool /Hot Tub/20 acres/Fiber Optic/Chef by Arrangement

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
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Modern Farm Home☀️2 hrs from NYC�Peaceful Oasis⚡️WIFI✔️Work remotely✨Clean, holiday rental in Old Chatham
Modern Farm Home☀️2 hrs from NYC�Peaceful Oasis⚡️WIFI✔️Work remotely✨Clean, holiday rental in Old Chatham
Modern Farm Home☀️2 hrs from NYC�Peaceful Oasis⚡️WIFI✔️Work remotely✨Clean, holiday rental in Old Chatham

Modern Farm Home☀️2 hrs from NYC�Peaceful Oasis⚡️WIFI✔️Work remotely✨Clean

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
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Quiet Get Away on the Lake! Kayaks,life vests ,Fishing Equipments ,golf clubs, holiday rental in Old Chatham
Quiet Get Away on the Lake! Kayaks,life vests ,Fishing Equipments ,golf clubs, holiday rental in Old Chatham
Quiet Get Away on the Lake! Kayaks,life vests ,Fishing Equipments ,golf clubs, holiday rental in Old Chatham

Quiet Get Away on the Lake! Kayaks,life vests ,Fishing Equipments ,golf clubs

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy yet spacious lakefront cottage, Ideal for all seasons, holiday rental in Old Chatham
Cozy yet spacious lakefront cottage, Ideal for all seasons, holiday rental in Old Chatham
Cozy yet spacious lakefront cottage, Ideal for all seasons, holiday rental in Old Chatham

Cozy yet spacious lakefront cottage, Ideal for all seasons

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!, holiday rental in Old Chatham
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!, holiday rental in Old Chatham
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!, holiday rental in Old Chatham

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Welcome to WIndswept Acres in the Berkshire Mts!, holiday rental in Old Chatham
Welcome to WIndswept Acres in the Berkshire Mts!, holiday rental in Old Chatham
Welcome to WIndswept Acres in the Berkshire Mts!, holiday rental in Old Chatham

Welcome to WIndswept Acres in the Berkshire Mts!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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A Beautiful Retreat In a Stunning Home and Landscaped Lawns, holiday rental in Old Chatham
A Beautiful Retreat In a Stunning Home and Landscaped Lawns, holiday rental in Old Chatham
A Beautiful Retreat In a Stunning Home and Landscaped Lawns, holiday rental in Old Chatham

A Beautiful Retreat In a Stunning Home and Landscaped Lawns

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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The Home in Malden Bridge, Columbia County, New York, holiday rental in Old Chatham
The Home in Malden Bridge, Columbia County, New York, holiday rental in Old Chatham
The Home in Malden Bridge, Columbia County, New York, holiday rental in Old Chatham

The Home in Malden Bridge, Columbia County, New York

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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18th Century Hilltop Home Nestled in Bucolic Oasis, holiday rental in Old Chatham
18th Century Hilltop Home Nestled in Bucolic Oasis, holiday rental in Old Chatham
18th Century Hilltop Home Nestled in Bucolic Oasis, holiday rental in Old Chatham

18th Century Hilltop Home Nestled in Bucolic Oasis

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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��HUDSON VALLEY ENTIRE HOUSE RENTAL��, holiday rental in Old Chatham
��HUDSON VALLEY ENTIRE HOUSE RENTAL��, holiday rental in Old Chatham
��HUDSON VALLEY ENTIRE HOUSE RENTAL��, holiday rental in Old Chatham

��HUDSON VALLEY ENTIRE HOUSE RENTAL��

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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4 Seasons of Bucolic Berkshire Beauty! Winter Ski and Snowboarding, holiday rental in Old Chatham
4 Seasons of Bucolic Berkshire Beauty! Winter Ski and Snowboarding, holiday rental in Old Chatham
4 Seasons of Bucolic Berkshire Beauty! Winter Ski and Snowboarding, holiday rental in Old Chatham

4 Seasons of Bucolic Berkshire Beauty! Winter Ski and Snowboarding

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Relax in the Country - Peace, quiet and family friendly, holiday rental in Old Chatham
Relax in the Country - Peace, quiet and family friendly, holiday rental in Old Chatham
Relax in the Country - Peace, quiet and family friendly, holiday rental in Old Chatham

Relax in the Country - Peace, quiet and family friendly

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Pure Berkshire Country Charm! Cozy Getaway  Fall Foliage Zoom Ready WiFi, holiday rental in Old Chatham
Pure Berkshire Country Charm! Cozy Getaway  Fall Foliage Zoom Ready WiFi, holiday rental in Old Chatham
Pure Berkshire Country Charm! Cozy Getaway  Fall Foliage Zoom Ready WiFi, holiday rental in Old Chatham

Pure Berkshire Country Charm! Cozy Getaway Fall Foliage Zoom Ready WiFi

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Amazing~Container-like Home~2 hrs from NYC & BOS~Waterfront~Clean~Wifi, holiday rental in Old Chatham
Amazing~Container-like Home~2 hrs from NYC & BOS~Waterfront~Clean~Wifi, holiday rental in Old Chatham
Amazing~Container-like Home~2 hrs from NYC & BOS~Waterfront~Clean~Wifi, holiday rental in Old Chatham

Amazing~Container-like Home~2 hrs from NYC & BOS~Waterfront~Clean~Wifi

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Secluded Family-Friendly Home, holiday rental in Old Chatham
Secluded Family-Friendly Home, holiday rental in Old Chatham
Secluded Family-Friendly Home, holiday rental in Old Chatham

Secluded Family-Friendly Home

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Newer Lakefront Home Near Berkshires wGourmet Kitchen, holiday rental in Old Chatham
Stunning Newer Lakefront Home Near Berkshires wGourmet Kitchen, holiday rental in Old Chatham
Stunning Newer Lakefront Home Near Berkshires wGourmet Kitchen, holiday rental in Old Chatham

Stunning Newer Lakefront Home Near Berkshires wGourmet Kitchen

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Chalet near 4 ski resorts with hot tub, holiday rental in Old Chatham
Chalet near 4 ski resorts with hot tub, holiday rental in Old Chatham
Chalet near 4 ski resorts with hot tub, holiday rental in Old Chatham

Chalet near 4 ski resorts with hot tub

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Cheerful 3BR Cottage on 1/4 mile private stream, holiday rental in Old Chatham
Cheerful 3BR Cottage on 1/4 mile private stream, holiday rental in Old Chatham
Cheerful 3BR Cottage on 1/4 mile private stream, holiday rental in Old Chatham

Cheerful 3BR Cottage on 1/4 mile private stream

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Martin Van Buren  lake cottage 1, holiday rental in Old Chatham
Martin Van Buren  lake cottage 1, holiday rental in Old Chatham
Martin Van Buren  lake cottage 1, holiday rental in Old Chatham

Martin Van Buren lake cottage 1

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Countryside House 30 mins to zipline/ski resorts, holiday rental in Old Chatham
Countryside House 30 mins to zipline/ski resorts, holiday rental in Old Chatham
Countryside House 30 mins to zipline/ski resorts, holiday rental in Old Chatham

Countryside House 30 mins to zipline/ski resorts

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Hudson: Martin Van Buren lake cottage lll (3), holiday rental in Old Chatham
Hudson: Martin Van Buren lake cottage lll (3), holiday rental in Old Chatham
Hudson: Martin Van Buren lake cottage lll (3), holiday rental in Old Chatham

Hudson: Martin Van Buren lake cottage lll (3)

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Quiet Country Cabin - adjacent to an 85 acre land preserve, holiday rental in Old Chatham
Quiet Country Cabin - adjacent to an 85 acre land preserve, holiday rental in Old Chatham
Quiet Country Cabin - adjacent to an 85 acre land preserve, holiday rental in Old Chatham

Quiet Country Cabin - adjacent to an 85 acre land preserve

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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2,000 sq ft loft located 'downtown' with access to dining..shops...movie theater, holiday rental in Old Chatham
2,000 sq ft loft located 'downtown' with access to dining..shops...movie theater, holiday rental in Old Chatham
2,000 sq ft loft located 'downtown' with access to dining..shops...movie theater, holiday rental in Old Chatham

2,000 sq ft loft located 'downtown' with access to dining..shops...movie theater

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Scandi-style modern cabin in Chatham: enjoy summer hygge in the woods, holiday rental in Old Chatham
Scandi-style modern cabin in Chatham: enjoy summer hygge in the woods, holiday rental in Old Chatham
Scandi-style modern cabin in Chatham: enjoy summer hygge in the woods, holiday rental in Old Chatham

Scandi-style modern cabin in Chatham: enjoy summer hygge in the woods

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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A cozy retreat to the farm life., holiday rental in Old Chatham
A cozy retreat to the farm life., holiday rental in Old Chatham
A cozy retreat to the farm life., holiday rental in Old Chatham

A cozy retreat to the farm life.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Berkshire Rural Retreat, holiday rental in Old Chatham
Berkshire Rural Retreat, holiday rental in Old Chatham
Berkshire Rural Retreat, holiday rental in Old Chatham

Berkshire Rural Retreat

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Charming Upstate Loft, holiday rental in Old Chatham
Charming Upstate Loft, holiday rental in Old Chatham
Charming Upstate Loft, holiday rental in Old Chatham

Charming Upstate Loft

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Four season lake side oasis in the berkshirkes, holiday rental in Old Chatham
Four season lake side oasis in the berkshirkes, holiday rental in Old Chatham
Four season lake side oasis in the berkshirkes, holiday rental in Old Chatham

Four season lake side oasis in the berkshirkes

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Star Gazer Farm, holiday rental in Old Chatham
Star Gazer Farm, holiday rental in Old Chatham
Star Gazer Farm, holiday rental in Old Chatham

Star Gazer Farm

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Welcome to the Red Bridge Cottage!, holiday rental in Old Chatham
Welcome to the Red Bridge Cottage!, holiday rental in Old Chatham
Welcome to the Red Bridge Cottage!, holiday rental in Old Chatham

Welcome to the Red Bridge Cottage!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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HGTV Tiny Home~2 hrs from NYC & BOS~Peaceful Oasis~Long-term stays~WIFI~Clean, holiday rental in Old Chatham
HGTV Tiny Home~2 hrs from NYC & BOS~Peaceful Oasis~Long-term stays~WIFI~Clean, holiday rental in Old Chatham
HGTV Tiny Home~2 hrs from NYC & BOS~Peaceful Oasis~Long-term stays~WIFI~Clean, holiday rental in Old Chatham

HGTV Tiny Home~2 hrs from NYC & BOS~Peaceful Oasis~Long-term stays~WIFI~Clean

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Hudson: Martin Van Buren lake cottage IIII, holiday rental in Old Chatham
Hudson: Martin Van Buren lake cottage IIII, holiday rental in Old Chatham
Hudson: Martin Van Buren lake cottage IIII, holiday rental in Old Chatham

Hudson: Martin Van Buren lake cottage IIII

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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A Haven of Rest in Stately Historic Home Cozy 2nd floor Suite., holiday rental in Old Chatham
A Haven of Rest in Stately Historic Home Cozy 2nd floor Suite., holiday rental in Old Chatham
A Haven of Rest in Stately Historic Home Cozy 2nd floor Suite., holiday rental in Old Chatham

A Haven of Rest in Stately Historic Home Cozy 2nd floor Suite.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Martin Van Buren lake Cottage 2, holiday rental in Old Chatham
Martin Van Buren lake Cottage 2, holiday rental in Old Chatham
Martin Van Buren lake Cottage 2, holiday rental in Old Chatham

Martin Van Buren lake Cottage 2

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Martin Van Buren historical hunting lodge / camp, holiday rental in Old Chatham
The Martin Van Buren historical hunting lodge / camp, holiday rental in Old Chatham
The Martin Van Buren historical hunting lodge / camp, holiday rental in Old Chatham

The Martin Van Buren historical hunting lodge / camp

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Tiny House(boat) on the Lake, holiday rental in Old Chatham
Tiny House(boat) on the Lake, holiday rental in Old Chatham
Tiny House(boat) on the Lake, holiday rental in Old Chatham

Tiny House(boat) on the Lake

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Dream getaway - mtn views, ski, pool, deck, nearby lake, work from home setups, holiday rental in Old Chatham
Dream getaway - mtn views, ski, pool, deck, nearby lake, work from home setups, holiday rental in Old Chatham
Dream getaway - mtn views, ski, pool, deck, nearby lake, work from home setups, holiday rental in Old Chatham

Dream getaway - mtn views, ski, pool, deck, nearby lake, work from home setups

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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