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Southbridge Holiday Apartments

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50 rentals in Southbridge.
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Country Estate With Pool, holiday rental in Southbridge
Country Estate With Pool, holiday rental in Southbridge
Country Estate With Pool, holiday rental in Southbridge

Country Estate With Pool

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 20
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Artist get away, holiday rental in Southbridge
Artist get away, holiday rental in Southbridge
Artist get away, holiday rental in Southbridge

Artist get away

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore, holiday rental in Southbridge
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore, holiday rental in Southbridge
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore, holiday rental in Southbridge

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Home with Stunning Views ....Great fishing, and Dog friendly �, holiday rental in Southbridge
Waterfront Home with Stunning Views ....Great fishing, and Dog friendly �, holiday rental in Southbridge
Waterfront Home with Stunning Views ....Great fishing, and Dog friendly �, holiday rental in Southbridge

Waterfront Home with Stunning Views ....Great fishing, and Dog friendly �

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Little Dipper Retreat Lakefront Cottage - Sandy Beach, Sunsets & Kayaks!, holiday rental in Southbridge
Little Dipper Retreat Lakefront Cottage - Sandy Beach, Sunsets & Kayaks!, holiday rental in Southbridge
Little Dipper Retreat Lakefront Cottage - Sandy Beach, Sunsets & Kayaks!, holiday rental in Southbridge

Little Dipper Retreat Lakefront Cottage - Sandy Beach, Sunsets & Kayaks!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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Weddings, Events and 'Farm-cations' on our Working Farm, holiday rental in Southbridge
Weddings, Events and 'Farm-cations' on our Working Farm, holiday rental in Southbridge
Weddings, Events and 'Farm-cations' on our Working Farm, holiday rental in Southbridge

Weddings, Events and 'Farm-cations' on our Working Farm

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!, holiday rental in Southbridge
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!, holiday rental in Southbridge
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!, holiday rental in Southbridge

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Charming Lakefront Cottage, holiday rental in Southbridge
Charming Lakefront Cottage, holiday rental in Southbridge
Charming Lakefront Cottage, holiday rental in Southbridge

Charming Lakefront Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!, holiday rental in Southbridge
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!, holiday rental in Southbridge
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!, holiday rental in Southbridge

Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest, holiday rental in Southbridge
Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest, holiday rental in Southbridge
Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest, holiday rental in Southbridge

Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Centrally Located, Dog Friendly, Vintage Lake House With Contemporary Amenities., holiday rental in Southbridge
Centrally Located, Dog Friendly, Vintage Lake House With Contemporary Amenities., holiday rental in Southbridge
Centrally Located, Dog Friendly, Vintage Lake House With Contemporary Amenities., holiday rental in Southbridge

Centrally Located, Dog Friendly, Vintage Lake House With Contemporary Amenities.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Hillside Lakehouse, Lake View,  Private Beach and Dock, holiday rental in Southbridge
Cozy Hillside Lakehouse, Lake View,  Private Beach and Dock, holiday rental in Southbridge
Cozy Hillside Lakehouse, Lake View,  Private Beach and Dock, holiday rental in Southbridge

Cozy Hillside Lakehouse, Lake View, Private Beach and Dock

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Waterfront - 2 BR, huge deck, gorgeous views, Lake Lashaway E. Brookfield, holiday rental in Southbridge
Waterfront - 2 BR, huge deck, gorgeous views, Lake Lashaway E. Brookfield, holiday rental in Southbridge
Waterfront - 2 BR, huge deck, gorgeous views, Lake Lashaway E. Brookfield, holiday rental in Southbridge

Waterfront - 2 BR, huge deck, gorgeous views, Lake Lashaway E. Brookfield

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Pet-friendly Waterfront Lake Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 7
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Your Own Private Luxury Resort - Sturbridge/Brimfield, MA, holiday rental in Southbridge
Your Own Private Luxury Resort - Sturbridge/Brimfield, MA, holiday rental in Southbridge
Your Own Private Luxury Resort - Sturbridge/Brimfield, MA, holiday rental in Southbridge

Your Own Private Luxury Resort - Sturbridge/Brimfield, MA

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Traditional Lake House near Old Sturbridge Village, holiday rental in Southbridge
Traditional Lake House near Old Sturbridge Village, holiday rental in Southbridge
Traditional Lake House near Old Sturbridge Village, holiday rental in Southbridge

Traditional Lake House near Old Sturbridge Village

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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A cozy cottage with charm and comfort, along with beauty and relaxation!, holiday rental in Southbridge
A cozy cottage with charm and comfort, along with beauty and relaxation!, holiday rental in Southbridge
A cozy cottage with charm and comfort, along with beauty and relaxation!, holiday rental in Southbridge

A cozy cottage with charm and comfort, along with beauty and relaxation!

Holiday Rental House
3 bedrooms
0 bathrooms
Sleeps 6
Match: Sleeps
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Webster Lake - Two Apartments, holiday rental in Southbridge
Webster Lake - Two Apartments, holiday rental in Southbridge
Webster Lake - Two Apartments, holiday rental in Southbridge

Webster Lake - Two Apartments

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lakeside Haven, holiday rental in Southbridge
Lakeside Haven, holiday rental in Southbridge
Lakeside Haven, holiday rental in Southbridge

Lakeside Haven

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Modern dog-friendly home on Webster Lake with water access & spectacular views, holiday rental in Southbridge
Modern dog-friendly home on Webster Lake with water access & spectacular views, holiday rental in Southbridge
Modern dog-friendly home on Webster Lake with water access & spectacular views, holiday rental in Southbridge

Modern dog-friendly home on Webster Lake with water access & spectacular views

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spacious Villa With Free Parking and King Beds, holiday rental in Southbridge
Spacious Villa With Free Parking and King Beds, holiday rental in Southbridge
Spacious Villa With Free Parking and King Beds, holiday rental in Southbridge

Spacious Villa With Free Parking and King Beds

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Wrecked at Ron’s, holiday rental in Southbridge
Wrecked at Ron’s, holiday rental in Southbridge
Wrecked at Ron’s, holiday rental in Southbridge

Wrecked at Ron’s

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Your Cottage on the Lake, holiday rental in Southbridge
Your Cottage on the Lake, holiday rental in Southbridge
Your Cottage on the Lake, holiday rental in Southbridge

Your Cottage on the Lake

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Abigail ‘s Nest, holiday rental in Southbridge
Abigail ‘s Nest, holiday rental in Southbridge
Abigail ‘s Nest, holiday rental in Southbridge

Abigail ‘s Nest

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Little House in the Big Woods, holiday rental in Southbridge
Little House in the Big Woods, holiday rental in Southbridge
Little House in the Big Woods, holiday rental in Southbridge

Little House in the Big Woods

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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*** SPECIAL WEEKLY AND WEEKEND RENTALS! NEGOTIABLE! PLEASE INQUIRE! ***, holiday rental in Southbridge
*** SPECIAL WEEKLY AND WEEKEND RENTALS! NEGOTIABLE! PLEASE INQUIRE! ***, holiday rental in Southbridge
*** SPECIAL WEEKLY AND WEEKEND RENTALS! NEGOTIABLE! PLEASE INQUIRE! ***, holiday rental in Southbridge

*** SPECIAL WEEKLY AND WEEKEND RENTALS! NEGOTIABLE! PLEASE INQUIRE! ***

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Delightful 3- bedroom house with backyard, holiday rental in Southbridge
Delightful 3- bedroom house with backyard, holiday rental in Southbridge
Delightful 3- bedroom house with backyard, holiday rental in Southbridge

Delightful 3- bedroom house with backyard

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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COMFY COUNTRY HOUSE, holiday rental in Southbridge
COMFY COUNTRY HOUSE, holiday rental in Southbridge
COMFY COUNTRY HOUSE, holiday rental in Southbridge

COMFY COUNTRY HOUSE

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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NEW! Vast Vintage-Style Home, 1/2 Mi to State Park, holiday rental in Southbridge
NEW! Vast Vintage-Style Home, 1/2 Mi to State Park, holiday rental in Southbridge
NEW! Vast Vintage-Style Home, 1/2 Mi to State Park, holiday rental in Southbridge

NEW! Vast Vintage-Style Home, 1/2 Mi to State Park

Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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NEW! Antique-Filled Home, 1/2 Mi to Woodstock Fair, holiday rental in Southbridge
NEW! Antique-Filled Home, 1/2 Mi to Woodstock Fair, holiday rental in Southbridge
NEW! Antique-Filled Home, 1/2 Mi to Woodstock Fair, holiday rental in Southbridge

NEW! Antique-Filled Home, 1/2 Mi to Woodstock Fair

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Woodsy Home w/ Hiking Trail Access On-Site!, holiday rental in Southbridge
NEW! Woodsy Home w/ Hiking Trail Access On-Site!, holiday rental in Southbridge
NEW! Woodsy Home w/ Hiking Trail Access On-Site!, holiday rental in Southbridge

NEW! Woodsy Home w/ Hiking Trail Access On-Site!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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NEW! Cozy Stafford Cabin, Near Reservoir & Beach!, holiday rental in Southbridge
NEW! Cozy Stafford Cabin, Near Reservoir & Beach!, holiday rental in Southbridge
NEW! Cozy Stafford Cabin, Near Reservoir & Beach!, holiday rental in Southbridge

NEW! Cozy Stafford Cabin, Near Reservoir & Beach!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Rustic Log Cabin on the Lake, holiday rental in Southbridge
Rustic Log Cabin on the Lake, holiday rental in Southbridge
Rustic Log Cabin on the Lake, holiday rental in Southbridge

Rustic Log Cabin on the Lake

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Majestic and UNFORGETTABLE House $******* upgrades and Tranquil Artistic Depth!!, holiday rental in Southbridge
Majestic and UNFORGETTABLE House $******* upgrades and Tranquil Artistic Depth!!, holiday rental in Southbridge
Majestic and UNFORGETTABLE House $******* upgrades and Tranquil Artistic Depth!!, holiday rental in Southbridge

Majestic and UNFORGETTABLE House $******* upgrades and Tranquil Artistic Depth!!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Ellen Elizabeth Estates of New England, holiday rental in Southbridge
Ellen Elizabeth Estates of New England, holiday rental in Southbridge
Ellen Elizabeth Estates of New England, holiday rental in Southbridge

Ellen Elizabeth Estates of New England

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy lake cottage with state boat launch access., holiday rental in Southbridge
Cozy lake cottage with state boat launch access., holiday rental in Southbridge
Cozy lake cottage with state boat launch access., holiday rental in Southbridge

Cozy lake cottage with state boat launch access.

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Spacious and new deluxe cabin in family campground in Northeastern CT, holiday rental in Southbridge
Spacious and new deluxe cabin in family campground in Northeastern CT, holiday rental in Southbridge
Spacious and new deluxe cabin in family campground in Northeastern CT, holiday rental in Southbridge

Spacious and new deluxe cabin in family campground in Northeastern CT

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Chalet Behind Famous Featherhill Mansion!!, holiday rental in Southbridge
Chalet Behind Famous Featherhill Mansion!!, holiday rental in Southbridge
Chalet Behind Famous Featherhill Mansion!!, holiday rental in Southbridge

Chalet Behind Famous Featherhill Mansion!!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Famous Estate Perfect for Events and Business retreats!!, holiday rental in Southbridge
Famous Estate Perfect for Events and Business retreats!!, holiday rental in Southbridge
Famous Estate Perfect for Events and Business retreats!!, holiday rental in Southbridge

Famous Estate Perfect for Events and Business retreats!!

Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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Antique farm house on pond, holiday rental in Southbridge
Antique farm house on pond, holiday rental in Southbridge
Antique farm house on pond, holiday rental in Southbridge

Antique farm house on pond

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Lake Cabin for Couples, holiday rental in Southbridge
Cozy Lake Cabin for Couples, holiday rental in Southbridge
Cozy Lake Cabin for Couples, holiday rental in Southbridge

Cozy Lake Cabin for Couples

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Webster Lake - 3BR / 2 BATH Apartment, holiday rental in Southbridge
Webster Lake - 3BR / 2 BATH Apartment, holiday rental in Southbridge
Webster Lake - 3BR / 2 BATH Apartment, holiday rental in Southbridge

Webster Lake - 3BR / 2 BATH Apartment

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Secluded 2 acre Lake Front Home!, holiday rental in Southbridge
Secluded 2 acre Lake Front Home!, holiday rental in Southbridge
Secluded 2 acre Lake Front Home!, holiday rental in Southbridge

Secluded 2 acre Lake Front Home!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful modern Lakehouse with private lake access for year-round getaways, holiday rental in Southbridge
Beautiful modern Lakehouse with private lake access for year-round getaways, holiday rental in Southbridge
Beautiful modern Lakehouse with private lake access for year-round getaways, holiday rental in Southbridge

Beautiful modern Lakehouse with private lake access for year-round getaways

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Little Cottage in Pomfret, holiday rental in Southbridge
Little Cottage in Pomfret, holiday rental in Southbridge
Little Cottage in Pomfret, holiday rental in Southbridge

Little Cottage in Pomfret

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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The Maybrook: Peaceful Getaway by a Lake, holiday rental in Southbridge
The Maybrook: Peaceful Getaway by a Lake, holiday rental in Southbridge
The Maybrook: Peaceful Getaway by a Lake, holiday rental in Southbridge

The Maybrook: Peaceful Getaway by a Lake

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Guesthouse on a Lake, holiday rental in Southbridge
Guesthouse on a Lake, holiday rental in Southbridge
Guesthouse on a Lake, holiday rental in Southbridge

Guesthouse on a Lake

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Gorgeous and spacious home, holiday rental in Southbridge
Gorgeous and spacious home, holiday rental in Southbridge
Gorgeous and spacious home, holiday rental in Southbridge

Gorgeous and spacious home

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Adorable a-frame cabin on the water, holiday rental in Southbridge
Adorable a-frame cabin on the water, holiday rental in Southbridge
Adorable a-frame cabin on the water, holiday rental in Southbridge

Adorable a-frame cabin on the water

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Leicester Lake Front Home, Come Relax, holiday rental in Southbridge
Leicester Lake Front Home, Come Relax, holiday rental in Southbridge
Leicester Lake Front Home, Come Relax, holiday rental in Southbridge

Leicester Lake Front Home, Come Relax

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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