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Roxbury Vacation Rentals

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50 rentals in Roxbury.
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Litchfield County Four Season Country Paradise, vacation rental in Roxbury
Litchfield County Four Season Country Paradise, vacation rental in Roxbury
Litchfield County Four Season Country Paradise, vacation rental in Roxbury

Litchfield County Four Season Country Paradise

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Charming country home in Roxbury, vacation rental in Roxbury
Charming country home in Roxbury, vacation rental in Roxbury
Charming country home in Roxbury, vacation rental in Roxbury

Charming country home in Roxbury

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

2 Bedroom Suite with Kitchen

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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100% ROXBURY PoshPadsCT 'PAINTER RIDGE' Mint 3BR, Pool, BBQ,Bikes 90-day minimum, vacation rental in Roxbury
100% ROXBURY PoshPadsCT 'PAINTER RIDGE' Mint 3BR, Pool, BBQ,Bikes 90-day minimum, vacation rental in Roxbury
100% ROXBURY PoshPadsCT 'PAINTER RIDGE' Mint 3BR, Pool, BBQ,Bikes 90-day minimum, vacation rental in Roxbury

100% ROXBURY PoshPadsCT 'PAINTER RIDGE' Mint 3BR, Pool, BBQ,Bikes 90-day minimum

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Nature & Luxury *Lavender Lake Est (Kosher optional), vacation rental in Roxbury
Nature & Luxury *Lavender Lake Est (Kosher optional), vacation rental in Roxbury
Nature & Luxury *Lavender Lake Est (Kosher optional), vacation rental in Roxbury

Nature & Luxury *Lavender Lake Est (Kosher optional)

Rental Home
7 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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100% Roxbury PoshPadsCT 'Tophet 3BR' Pool/Spa, Bikes, BBQ, FP, 60-night Minimum, vacation rental in Roxbury
100% Roxbury PoshPadsCT 'Tophet 3BR' Pool/Spa, Bikes, BBQ, FP, 60-night Minimum, vacation rental in Roxbury
100% Roxbury PoshPadsCT 'Tophet 3BR' Pool/Spa, Bikes, BBQ, FP, 60-night Minimum, vacation rental in Roxbury

100% Roxbury PoshPadsCT 'Tophet 3BR' Pool/Spa, Bikes, BBQ, FP, 60-night Minimum

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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100% Roxbury 'Tophet Pool Barn' PoshPadsCT 1 BR Loft, Pool, BBQ, 90-day minimum, vacation rental in Roxbury
100% Roxbury 'Tophet Pool Barn' PoshPadsCT 1 BR Loft, Pool, BBQ, 90-day minimum, vacation rental in Roxbury
100% Roxbury 'Tophet Pool Barn' PoshPadsCT 1 BR Loft, Pool, BBQ, 90-day minimum, vacation rental in Roxbury

100% Roxbury 'Tophet Pool Barn' PoshPadsCT 1 BR Loft, Pool, BBQ, 90-day minimum

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Country Chic Getaway, vacation rental in Roxbury
Country Chic Getaway, vacation rental in Roxbury
Country Chic Getaway, vacation rental in Roxbury

Country Chic Getaway

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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'Tunnel Rd' Mint Reno 4-BR Best Best 100% Roxbury Location PoshPadsCT on Shepaug, vacation rental in Roxbury
'Tunnel Rd' Mint Reno 4-BR Best Best 100% Roxbury Location PoshPadsCT on Shepaug, vacation rental in Roxbury
'Tunnel Rd' Mint Reno 4-BR Best Best 100% Roxbury Location PoshPadsCT on Shepaug, vacation rental in Roxbury

'Tunnel Rd' Mint Reno 4-BR Best Best 100% Roxbury Location PoshPadsCT on Shepaug

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Cottage on Quiet Lake, private dock, private beach area, boat use, vacation rental in Roxbury
Lakefront Cottage on Quiet Lake, private dock, private beach area, boat use, vacation rental in Roxbury
Lakefront Cottage on Quiet Lake, private dock, private beach area, boat use, vacation rental in Roxbury

Lakefront Cottage on Quiet Lake, private dock, private beach area, boat use

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Quaint cottage located directly on Long Meadow Pond, vacation rental in Roxbury
Quaint cottage located directly on Long Meadow Pond, vacation rental in Roxbury
Quaint cottage located directly on Long Meadow Pond, vacation rental in Roxbury

Quaint cottage located directly on Long Meadow Pond

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Private Annex/Former Artist Studo, vacation rental in Roxbury
Private Annex/Former Artist Studo, vacation rental in Roxbury
Private Annex/Former Artist Studo, vacation rental in Roxbury

Private Annex/Former Artist Studo

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Modern Architectural Home in Washington, Ct. 5 Star with video, vacation rental in Roxbury
Beautiful Modern Architectural Home in Washington, Ct. 5 Star with video, vacation rental in Roxbury
Beautiful Modern Architectural Home in Washington, Ct. 5 Star with video, vacation rental in Roxbury

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Renovated, one level home in an excellent location. Walk to the beach!, vacation rental in Roxbury
Renovated, one level home in an excellent location. Walk to the beach!, vacation rental in Roxbury
Renovated, one level home in an excellent location. Walk to the beach!, vacation rental in Roxbury

Renovated, one level home in an excellent location. Walk to the beach!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Direct Water Front Home, vacation rental in Roxbury
Direct Water Front Home, vacation rental in Roxbury
Direct Water Front Home, vacation rental in Roxbury

Direct Water Front Home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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1905 Remodeled New England Cape Quintessential Connecticut Countryside Getaway, vacation rental in Roxbury
1905 Remodeled New England Cape Quintessential Connecticut Countryside Getaway, vacation rental in Roxbury
1905 Remodeled New England Cape Quintessential Connecticut Countryside Getaway, vacation rental in Roxbury

1905 Remodeled New England Cape Quintessential Connecticut Countryside Getaway

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants, vacation rental in Roxbury
Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants, vacation rental in Roxbury
Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants, vacation rental in Roxbury

Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Direct Waterfront Cottage On Candlewood Lake - Sleeps 6, vacation rental in Roxbury
Direct Waterfront Cottage On Candlewood Lake - Sleeps 6, vacation rental in Roxbury
Direct Waterfront Cottage On Candlewood Lake - Sleeps 6, vacation rental in Roxbury

Direct Waterfront Cottage On Candlewood Lake - Sleeps 6

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

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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1795 Carriage House set in 2 acres of Lawns and gardens, vacation rental in Roxbury
1795 Carriage House set in 2 acres of Lawns and gardens, vacation rental in Roxbury
1795 Carriage House set in 2 acres of Lawns and gardens, vacation rental in Roxbury

1795 Carriage House set in 2 acres of Lawns and gardens

Rental Home
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Direct Lakefront Home on Lake Lillinonah with Elevator Access, vacation rental in Roxbury
Direct Lakefront Home on Lake Lillinonah with Elevator Access, vacation rental in Roxbury
Direct Lakefront Home on Lake Lillinonah with Elevator Access, vacation rental in Roxbury

Direct Lakefront Home on Lake Lillinonah with Elevator Access

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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New Listing-Best Location on Candlewood Lakefront Home -1 Acre w/ Dock, vacation rental in Roxbury
New Listing-Best Location on Candlewood Lakefront Home -1 Acre w/ Dock, vacation rental in Roxbury
New Listing-Best Location on Candlewood Lakefront Home -1 Acre w/ Dock, vacation rental in Roxbury

New Listing-Best Location on Candlewood Lakefront Home -1 Acre w/ Dock

Rental Home
6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Stately 1792 retreat on 23 acres, chic modern renovation with gunite pool, vacation rental in Roxbury
Stately 1792 retreat on 23 acres, chic modern renovation with gunite pool, vacation rental in Roxbury
Stately 1792 retreat on 23 acres, chic modern renovation with gunite pool, vacation rental in Roxbury

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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100% WASHINGTON! PoshPadsCT 'SHEARER RD' Mint 3BR, Pool, BBQ, 2FPs 90-day min., vacation rental in Roxbury
100% WASHINGTON! PoshPadsCT 'SHEARER RD' Mint 3BR, Pool, BBQ, 2FPs 90-day min., vacation rental in Roxbury
100% WASHINGTON! PoshPadsCT 'SHEARER RD' Mint 3BR, Pool, BBQ, 2FPs 90-day min., vacation rental in Roxbury

100% WASHINGTON! PoshPadsCT 'SHEARER RD' Mint 3BR, Pool, BBQ, 2FPs 90-day min.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Mabels Hollow Farm, En suite bedroom farm stay,, vacation rental in Roxbury
Mabels Hollow Farm, En suite bedroom farm stay,, vacation rental in Roxbury
Mabels Hollow Farm, En suite bedroom farm stay,, vacation rental in Roxbury

Mabels Hollow Farm, En suite bedroom farm stay,

Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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NEW! Long Meadow Manor, POOL is OPEN for summer!, vacation rental in Roxbury
NEW! Long Meadow Manor, POOL is OPEN for summer!, vacation rental in Roxbury
NEW! Long Meadow Manor, POOL is OPEN for summer!, vacation rental in Roxbury

NEW! Long Meadow Manor, POOL is OPEN for summer!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Candlewood Lake Beauty - Home is right on the water! - 5 bedrooms, sleeps 12, vacation rental in Roxbury
Candlewood Lake Beauty - Home is right on the water! - 5 bedrooms, sleeps 12, vacation rental in Roxbury
Candlewood Lake Beauty - Home is right on the water! - 5 bedrooms, sleeps 12, vacation rental in Roxbury

Candlewood Lake Beauty - Home is right on the water! - 5 bedrooms, sleeps 12

Rental Home
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Barn Apartment Hideaway, vacation rental in Roxbury
Barn Apartment Hideaway, vacation rental in Roxbury
Barn Apartment Hideaway, vacation rental in Roxbury

Barn Apartment Hideaway

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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STEPPING STONES, Candlewood Lake Cottage, 3BR 2BA w/ Hot Tub & Pool Table!, vacation rental in Roxbury
STEPPING STONES, Candlewood Lake Cottage, 3BR 2BA w/ Hot Tub & Pool Table!, vacation rental in Roxbury
STEPPING STONES, Candlewood Lake Cottage, 3BR 2BA w/ Hot Tub & Pool Table!, vacation rental in Roxbury

STEPPING STONES, Candlewood Lake Cottage, 3BR 2BA w/ Hot Tub & Pool Table!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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100% WASHINGTON PoshPadsCT 'SOUTH ST' Mint 4 BR, Heated Pool, BBQ, Bikes, vacation rental in Roxbury
100% WASHINGTON PoshPadsCT 'SOUTH ST' Mint 4 BR, Heated Pool, BBQ, Bikes, vacation rental in Roxbury
100% WASHINGTON PoshPadsCT 'SOUTH ST' Mint 4 BR, Heated Pool, BBQ, Bikes, vacation rental in Roxbury

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Original house with modern kitchen & baths; lawns & greenhouse for celebrations, vacation rental in Roxbury
Original house with modern kitchen & baths; lawns & greenhouse for celebrations, vacation rental in Roxbury
Original house with modern kitchen & baths; lawns & greenhouse for celebrations, vacation rental in Roxbury

Original house with modern kitchen & baths; lawns & greenhouse for celebrations

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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100% WASHINGTON GREEN - Zoom in Map! PoshPadsCT KIRBY ROAD - 3BR Perfect Setting, vacation rental in Roxbury
100% WASHINGTON GREEN - Zoom in Map! PoshPadsCT KIRBY ROAD - 3BR Perfect Setting, vacation rental in Roxbury
100% WASHINGTON GREEN - Zoom in Map! PoshPadsCT KIRBY ROAD - 3BR Perfect Setting, vacation rental in Roxbury

100% WASHINGTON GREEN - Zoom in Map! PoshPadsCT KIRBY ROAD - 3BR Perfect Setting

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Still Waters Retreat, vacation rental in Roxbury
Still Waters Retreat, vacation rental in Roxbury
Still Waters Retreat, vacation rental in Roxbury

Still Waters Retreat

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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100% WASHINGTON! (Zoom in Map++) PoshPadsCT 'SUNNY RIDGE' 8-BR Estate, Pool, BBQ, vacation rental in Roxbury
100% WASHINGTON! (Zoom in Map++) PoshPadsCT 'SUNNY RIDGE' 8-BR Estate, Pool, BBQ, vacation rental in Roxbury
100% WASHINGTON! (Zoom in Map++) PoshPadsCT 'SUNNY RIDGE' 8-BR Estate, Pool, BBQ, vacation rental in Roxbury

100% WASHINGTON! (Zoom in Map++) PoshPadsCT 'SUNNY RIDGE' 8-BR Estate, Pool, BBQ

Rental Home
8 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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Candlewood Lake lakefront property, vacation rental in Roxbury
Candlewood Lake lakefront property, vacation rental in Roxbury
Candlewood Lake lakefront property, vacation rental in Roxbury

Candlewood Lake lakefront property

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lake Summer Home with a Dog (Monthly rental only), vacation rental in Roxbury
Lake Summer Home with a Dog (Monthly rental only), vacation rental in Roxbury
Lake Summer Home with a Dog (Monthly rental only), vacation rental in Roxbury

Lake Summer Home with a Dog (Monthly rental only)

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Perfect entertainment home, 20 x 40 in-ground pool pool table, bar, gym, & more, vacation rental in Roxbury
Perfect entertainment home, 20 x 40 in-ground pool pool table, bar, gym, & more, vacation rental in Roxbury
Perfect entertainment home, 20 x 40 in-ground pool pool table, bar, gym, & more, vacation rental in Roxbury

Perfect entertainment home, 20 x 40 in-ground pool pool table, bar, gym, & more

Rental Home
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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100% WASHINGTON! PoshPadsCT'Calhoun' 4BR, Views!,Meadows,Pool,25Acres, 90day min, vacation rental in Roxbury
100% WASHINGTON! PoshPadsCT'Calhoun' 4BR, Views!,Meadows,Pool,25Acres, 90day min, vacation rental in Roxbury
100% WASHINGTON! PoshPadsCT'Calhoun' 4BR, Views!,Meadows,Pool,25Acres, 90day min, vacation rental in Roxbury

100% WASHINGTON! PoshPadsCT'Calhoun' 4BR, Views!,Meadows,Pool,25Acres, 90day min

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Country Condo ( 3 Months mimimun ), vacation rental in Roxbury
Country Condo ( 3 Months mimimun ), vacation rental in Roxbury
Country Condo ( 3 Months mimimun ), vacation rental in Roxbury

Country Condo ( 3 Months mimimun )

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Country Estate with Heated Pool, vacation rental in Roxbury
Beautiful Country Estate with Heated Pool, vacation rental in Roxbury
Beautiful Country Estate with Heated Pool, vacation rental in Roxbury

Beautiful Country Estate with Heated Pool

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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100% Washington! 'Kielwasser Barn'  PoshPadsCT Pool, 4 FPs, Bikes 90-Day Minimum, vacation rental in Roxbury
100% Washington! 'Kielwasser Barn'  PoshPadsCT Pool, 4 FPs, Bikes 90-Day Minimum, vacation rental in Roxbury
100% Washington! 'Kielwasser Barn'  PoshPadsCT Pool, 4 FPs, Bikes 90-Day Minimum, vacation rental in Roxbury

100% Washington! 'Kielwasser Barn' PoshPadsCT Pool, 4 FPs, Bikes 90-Day Minimum

Rental Home
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Beautiful country home steps from Candlewood Lake, vacation rental in Roxbury
Beautiful country home steps from Candlewood Lake, vacation rental in Roxbury
Beautiful country home steps from Candlewood Lake, vacation rental in Roxbury

Beautiful country home steps from Candlewood Lake

Rental Home
3 bedrooms
0 bathrooms
Sleeps 8
Match: Sleeps
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Serene haven in the country, vacation rental in Roxbury
Serene haven in the country, vacation rental in Roxbury
Serene haven in the country, vacation rental in Roxbury

Serene haven in the country

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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A Haven in the Country--just renovated, vacation rental in Roxbury
A Haven in the Country--just renovated, vacation rental in Roxbury
A Haven in the Country--just renovated, vacation rental in Roxbury

A Haven in the Country--just renovated

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Mabels Hollow Farm, In the heart of Litchfield County, vacation rental in Roxbury
Mabels Hollow Farm, In the heart of Litchfield County, vacation rental in Roxbury
Mabels Hollow Farm, In the heart of Litchfield County, vacation rental in Roxbury

Mabels Hollow Farm, In the heart of Litchfield County

Rental Home
5 bedrooms
6 bathrooms
Sleeps 6
Match: Sleeps
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NEW LISTING! Waterfront Paradise on Candlewood Lake, vacation rental in Roxbury
NEW LISTING! Waterfront Paradise on Candlewood Lake, vacation rental in Roxbury
NEW LISTING! Waterfront Paradise on Candlewood Lake, vacation rental in Roxbury

NEW LISTING! Waterfront Paradise on Candlewood Lake

Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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100% Washington 45 Calhoun PoshPadsCT - Gardens, Pool, BBQ, Bikes 90-day Minimum, vacation rental in Roxbury
100% Washington 45 Calhoun PoshPadsCT - Gardens, Pool, BBQ, Bikes 90-day Minimum, vacation rental in Roxbury
100% Washington 45 Calhoun PoshPadsCT - Gardens, Pool, BBQ, Bikes 90-day Minimum, vacation rental in Roxbury

100% Washington 45 Calhoun PoshPadsCT - Gardens, Pool, BBQ, Bikes 90-day Minimum

Rental Home
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful Lakefront Home in Brookfield, vacation rental in Roxbury
Beautiful Lakefront Home in Brookfield, vacation rental in Roxbury
Beautiful Lakefront Home in Brookfield, vacation rental in Roxbury

Beautiful Lakefront Home in Brookfield

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Summer Cottage - Bike to Lake Waramaug, vacation rental in Roxbury
Summer Cottage - Bike to Lake Waramaug, vacation rental in Roxbury
Summer Cottage - Bike to Lake Waramaug, vacation rental in Roxbury

Summer Cottage - Bike to Lake Waramaug

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Night Light Lake House, vacation rental in Roxbury
Night Light Lake House, vacation rental in Roxbury
Night Light Lake House, vacation rental in Roxbury

Night Light Lake House

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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