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Roxbury Holiday Rentals

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50 rentals in Roxbury.
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Charming country home in Roxbury, holiday rental in Roxbury

Charming country home in Roxbury

3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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2 Bedroom Suite with Kitchen, holiday rental in Roxbury

2 Bedroom Suite with Kitchen

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Nature & Luxury *Lavender Lake Est (Kosher optional), holiday rental in Roxbury

Nature & Luxury *Lavender Lake Est (Kosher optional)

7 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Newly Renovated 18th Century Cottage On 4 Acres, holiday rental in Roxbury

Newly Renovated 18th Century Cottage On 4 Acres

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can Accommodate Six., holiday rental in Roxbury

Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can Accommodate Six.

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Peaceful Candlewood  lake/woods retreat., holiday rental in Roxbury

Peaceful Candlewood lake/woods retreat.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Historic Warren/Kent Home, holiday rental in Roxbury

Historic Warren/Kent Home

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Modern Architectural Home in Washington, Ct. 5 Star with video, holiday rental in Roxbury

Beautiful Modern Architectural Home in Washington, Ct. 5 Star with video

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Exceptional Beauty On The Water!! Candlewood Lake - Danbury, CT, holiday rental in Roxbury

Exceptional Beauty On The Water!! Candlewood Lake - Danbury, CT

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Private Annex/Former Artist Studo, holiday rental in Roxbury

Private Annex/Former Artist Studo

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Direct Water Front Home, holiday rental in Roxbury

Direct Water Front Home

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Litchfield Hills Hideaway, holiday rental in Roxbury

Litchfield Hills Hideaway

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Expansive Countryside House, 7 Serene Acres with Pond & Woods, holiday rental in Roxbury

Expansive Countryside House, 7 Serene Acres with Pond & Woods

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lakefront Luxury Retreat on Candlewood Lake, holiday rental in Roxbury

Lakefront Luxury Retreat on Candlewood Lake

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Quaint cottage located directly on Long Meadow Pond, holiday rental in Roxbury

Quaint cottage located directly on Long Meadow Pond

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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1905 Remodeled New England Cape Quintessential Connecticut Countryside Getaway, holiday rental in Roxbury

1905 Remodeled New England Cape Quintessential Connecticut Countryside Getaway

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Lookout on Candlewood Lake, holiday rental in Roxbury

The Lookout on Candlewood Lake

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Modern cottage on the Housatonic River, holiday rental in Roxbury

Modern cottage on the Housatonic River

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cottage in Lake Community - Blocked for bathroom renovation (2 bed 2 bath), holiday rental in Roxbury

Cottage in Lake Community - Blocked for bathroom renovation (2 bed 2 bath)

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lakefront home with private dock, kayaks,  and paddleboard.  Boat rentals nearby, holiday rental in Roxbury

Lakefront home with private dock, kayaks, and paddleboard. Boat rentals nearby

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Level, direct lakefront, expansive western views, beach on Candlewood Lake, holiday rental in Roxbury

Level, direct lakefront, expansive western views, beach on Candlewood Lake

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Warren country retreat, holiday rental in Roxbury

Warren country retreat

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Direct Waterfront on Candlewood Lake with/ boat slip & expansive outdoor kitchen, holiday rental in Roxbury

Direct Waterfront on Candlewood Lake with/ boat slip & expansive outdoor kitchen

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront House on Lake Waramaug!, holiday rental in Roxbury

Waterfront House on Lake Waramaug!

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Waterfront Retreat on Bantam Lake with Private Beach - Winter Ski Getaway, holiday rental in Roxbury

Waterfront Retreat on Bantam Lake with Private Beach - Winter Ski Getaway

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Stunning Waterfront Lake House with Amazing Views, holiday rental in Roxbury

Stunning Waterfront Lake House with Amazing Views

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Direct Lakefront Home on Lake Lillinonah with Elevator Access, holiday rental in Roxbury

Direct Lakefront Home on Lake Lillinonah with Elevator Access

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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SUN HILL FARM 1/4 MILE FROM LAKE WARAMAU, holiday rental in Roxbury

SUN HILL FARM 1/4 MILE FROM LAKE WARAMAU

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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3 BR Cabin in Private Candlewood Lake Community, holiday rental in Roxbury

3 BR Cabin in Private Candlewood Lake Community

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Rustic Country Beach Cottage Candlewood Lake, holiday rental in Roxbury

Rustic Country Beach Cottage Candlewood Lake

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stately 1792 retreat on 23 acres, chic modern renovation with gunite pool, holiday rental in Roxbury

Stately 1792 retreat on 23 acres, chic modern renovation with gunite pool

3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Mabels Hollow Farm, En suite bedroom farm stay,, holiday rental in Roxbury

Mabels Hollow Farm, En suite bedroom farm stay,

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Cozy Litchfield House w/ Fenced-In Yard & Fire Pit, holiday rental in Roxbury

Cozy Litchfield House w/ Fenced-In Yard & Fire Pit

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Country Estate newly renovated that sleeps 16!, holiday rental in Roxbury

Country Estate newly renovated that sleeps 16!

5 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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NEW! Woodland Retreat w/ Pool & Near Wineries!, holiday rental in Roxbury

NEW! Woodland Retreat w/ Pool & Near Wineries!

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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100% WASHINGTON PoshPadsCT 'SOUTH ST' Mint 4 BR, Heated Pool, BBQ, Bikes, holiday rental in Roxbury

100% WASHINGTON PoshPadsCT 'SOUTH ST' Mint 4 BR, Heated Pool, BBQ, Bikes

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Dainty New Preston Cottage w/ Dock & Lake Views!, holiday rental in Roxbury

Dainty New Preston Cottage w/ Dock & Lake Views!

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Sherman Home w/Lakefront Deck & Swimming Dock, holiday rental in Roxbury

Sherman Home w/Lakefront Deck & Swimming Dock

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lake Summer Home with a Dog (Monthly rental only), holiday rental in Roxbury

Lake Summer Home with a Dog (Monthly rental only)

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Country Condo ( 3 Months mimimun ), holiday rental in Roxbury

Country Condo ( 3 Months mimimun )

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Serene haven in the country, holiday rental in Roxbury

Serene haven in the country

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Direct Lakefront, Bantam Lake, Private Deer Island, holiday rental in Roxbury

Direct Lakefront, Bantam Lake, Private Deer Island

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Family Getaway w/ Fireplace in Sherman on 4 Acres!, holiday rental in Roxbury

Family Getaway w/ Fireplace in Sherman on 4 Acres!

7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Flat - Pals - 2 Bedrooms, 1 Bathrooms, Lift, Urbanizacion, holiday rental in Roxbury

Flat - Pals - 2 Bedrooms, 1 Bathrooms, Lift, Urbanizacion

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Newly Listed Lake House! Private Beach on Candlewood Lake, New Construction Beau, holiday rental in Roxbury

Newly Listed Lake House! Private Beach on Candlewood Lake, New Construction Beau

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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NEW! 2,438 Sq Ft Washington House - Pets Welcome!, holiday rental in Roxbury

NEW! 2,438 Sq Ft Washington House - Pets Welcome!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Whimsical Cottage in Washington w/ Fire Pit!, holiday rental in Roxbury

NEW! Whimsical Cottage in Washington w/ Fire Pit!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Chic & Spacious Riverfront Reprieve w/ Dock!, holiday rental in Roxbury

NEW! Chic & Spacious Riverfront Reprieve w/ Dock!

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Night Light Lake House, holiday rental in Roxbury

Night Light Lake House

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Updated 200-Yr-Old Home w/ Silo Living Space!, holiday rental in Roxbury

NEW! Updated 200-Yr-Old Home w/ Silo Living Space!

1 bedroom
3 bathrooms
Sleeps 8
Match: Sleeps
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