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Winchester Holiday Apartments

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50 rentals in Winchester.
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Stay at a Craft Brewery in Winchester NH Close to mountains, hiking, & breweries, holiday rental in Winchester
Stay at a Craft Brewery in Winchester NH Close to mountains, hiking, & breweries, holiday rental in Winchester
Stay at a Craft Brewery in Winchester NH Close to mountains, hiking, & breweries, holiday rental in Winchester

Stay at a Craft Brewery in Winchester NH Close to mountains, hiking, & breweries

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Magical Lakefront Home on Forest Lake, holiday rental in Winchester
Magical Lakefront Home on Forest Lake, holiday rental in Winchester
Magical Lakefront Home on Forest Lake, holiday rental in Winchester

Magical Lakefront Home on Forest Lake

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Beautiful Lake Side Getaway, Quiet, and Peaceful, holiday rental in Winchester
Beautiful Lake Side Getaway, Quiet, and Peaceful, holiday rental in Winchester
Beautiful Lake Side Getaway, Quiet, and Peaceful, holiday rental in Winchester

Beautiful Lake Side Getaway, Quiet, and Peaceful

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stay at a Craft Brewery, holiday rental in Winchester
Stay at a Craft Brewery, holiday rental in Winchester
Stay at a Craft Brewery, holiday rental in Winchester

Stay at a Craft Brewery

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stunning Forest Lake Home with Hot Tub open all Yr, holiday rental in Winchester
Stunning Forest Lake Home with Hot Tub open all Yr, holiday rental in Winchester
Stunning Forest Lake Home with Hot Tub open all Yr, holiday rental in Winchester

Stunning Forest Lake Home with Hot Tub open all Yr

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Lakefront Retreat in Winchester, Getaway Ready and Fully Equipped, holiday rental in Winchester
Lakefront Retreat in Winchester, Getaway Ready and Fully Equipped, holiday rental in Winchester
Lakefront Retreat in Winchester, Getaway Ready and Fully Equipped, holiday rental in Winchester

Lakefront Retreat in Winchester, Getaway Ready and Fully Equipped

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
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Large modern house with huge open great room and four large bedrooms with baths, holiday rental in Winchester
Large modern house with huge open great room and four large bedrooms with baths, holiday rental in Winchester
Large modern house with huge open great room and four large bedrooms with baths, holiday rental in Winchester

Large modern house with huge open great room and four large bedrooms with baths

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Serenity Cottage in Southern Vermont…, holiday rental in Winchester
Serenity Cottage in Southern Vermont…, holiday rental in Winchester
Serenity Cottage in Southern Vermont…, holiday rental in Winchester

Serenity Cottage in Southern Vermont…

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Sprawling, secluded gourmand's large cottage at base of Mt Monadnock, holiday rental in Winchester
Sprawling, secluded gourmand's large cottage at base of Mt Monadnock, holiday rental in Winchester
Sprawling, secluded gourmand's large cottage at base of Mt Monadnock, holiday rental in Winchester

Sprawling, secluded gourmand's large cottage at base of Mt Monadnock

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
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Peaceful, Beautiful, Comfortable Modern Cape With Mountain Views, holiday rental in Winchester
Peaceful, Beautiful, Comfortable Modern Cape With Mountain Views, holiday rental in Winchester
Peaceful, Beautiful, Comfortable Modern Cape With Mountain Views, holiday rental in Winchester

Peaceful, Beautiful, Comfortable Modern Cape With Mountain Views

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
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The Comforts of Home..., holiday rental in Winchester
The Comforts of Home..., holiday rental in Winchester
The Comforts of Home..., holiday rental in Winchester

The Comforts of Home...

Holiday Rental House
3 bedrooms
0 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful lakefront log home nestled in the pines, holiday rental in Winchester
Beautiful lakefront log home nestled in the pines, holiday rental in Winchester
Beautiful lakefront log home nestled in the pines, holiday rental in Winchester

Beautiful lakefront log home nestled in the pines

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded Architect designed House - Monadnock Region - Great Escape, holiday rental in Winchester
Secluded Architect designed House - Monadnock Region - Great Escape, holiday rental in Winchester
Secluded Architect designed House - Monadnock Region - Great Escape, holiday rental in Winchester

Secluded Architect designed House - Monadnock Region - Great Escape

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Romantic Rock River Cottage with Hot Tub, Fireplace & Beach - Newfane VT, holiday rental in Winchester
Romantic Rock River Cottage with Hot Tub, Fireplace & Beach - Newfane VT, holiday rental in Winchester
Romantic Rock River Cottage with Hot Tub, Fireplace & Beach - Newfane VT, holiday rental in Winchester

Romantic Rock River Cottage with Hot Tub, Fireplace & Beach - Newfane VT

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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Charming Lakeside Cabin on Pristine Swanzey Lake, holiday rental in Winchester
Charming Lakeside Cabin on Pristine Swanzey Lake, holiday rental in Winchester
Charming Lakeside Cabin on Pristine Swanzey Lake, holiday rental in Winchester

Charming Lakeside Cabin on Pristine Swanzey Lake

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Laurel Lake Cottage in New Hampshire, holiday rental in Winchester
Laurel Lake Cottage in New Hampshire, holiday rental in Winchester
Laurel Lake Cottage in New Hampshire, holiday rental in Winchester

Laurel Lake Cottage in New Hampshire

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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3 BR Farmhouse on 100 Acre Farm Near Vermont, holiday rental in Winchester
3 BR Farmhouse on 100 Acre Farm Near Vermont, holiday rental in Winchester
3 BR Farmhouse on 100 Acre Farm Near Vermont, holiday rental in Winchester

3 BR Farmhouse on 100 Acre Farm Near Vermont

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Pet And Family Friendly Hilltop House In Putney Vermont, holiday rental in Winchester
Pet And Family Friendly Hilltop House In Putney Vermont, holiday rental in Winchester
Pet And Family Friendly Hilltop House In Putney Vermont, holiday rental in Winchester

Pet And Family Friendly Hilltop House In Putney Vermont

Holiday Rental House
0 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Fishing Cottage, A Sweetwater Stay, holiday rental in Winchester
The Fishing Cottage, A Sweetwater Stay, holiday rental in Winchester
The Fishing Cottage, A Sweetwater Stay, holiday rental in Winchester

The Fishing Cottage, A Sweetwater Stay

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Tyler House - 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford, holiday rental in Winchester
Tyler House - 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford, holiday rental in Winchester
Tyler House - 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford, holiday rental in Winchester

Tyler House - 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
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Vacationer's oasis on the waterfront of picturesque Pearly Pond., holiday rental in Winchester
Vacationer's oasis on the waterfront of picturesque Pearly Pond., holiday rental in Winchester
Vacationer's oasis on the waterfront of picturesque Pearly Pond., holiday rental in Winchester

Vacationer's oasis on the waterfront of picturesque Pearly Pond.

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious Lakeside Waterfront Summer Cottage, holiday rental in Winchester
Spacious Lakeside Waterfront Summer Cottage, holiday rental in Winchester
Spacious Lakeside Waterfront Summer Cottage, holiday rental in Winchester

Spacious Lakeside Waterfront Summer Cottage

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Quiet Vermont Home Close To Everything, holiday rental in Winchester
Quiet Vermont Home Close To Everything, holiday rental in Winchester
Quiet Vermont Home Close To Everything, holiday rental in Winchester

Quiet Vermont Home Close To Everything

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lakefront all-season beauty and fun!, holiday rental in Winchester
Lakefront all-season beauty and fun!, holiday rental in Winchester
Lakefront all-season beauty and fun!, holiday rental in Winchester

Lakefront all-season beauty and fun!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Vermont Log Cabin available for weekend and weekly, holiday rental in Winchester
Vermont Log Cabin available for weekend and weekly, holiday rental in Winchester
Vermont Log Cabin available for weekend and weekly, holiday rental in Winchester

Vermont Log Cabin available for weekend and weekly

Cabin Holiday Rental
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Escape to peaceful Putney Vermont, holiday rental in Winchester
Escape to peaceful Putney Vermont, holiday rental in Winchester
Escape to peaceful Putney Vermont, holiday rental in Winchester

Escape to peaceful Putney Vermont

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Main House - Relax and enjoy the scenery, go and swim, fish or start your boat, holiday rental in Winchester
Main House - Relax and enjoy the scenery, go and swim, fish or start your boat, holiday rental in Winchester
Main House - Relax and enjoy the scenery, go and swim, fish or start your boat, holiday rental in Winchester

Main House - Relax and enjoy the scenery, go and swim, fish or start your boat

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Cozy Waterfront Cottage Only Minutes from Downtown Keene, NH!, holiday rental in Winchester
Cozy Waterfront Cottage Only Minutes from Downtown Keene, NH!, holiday rental in Winchester
Cozy Waterfront Cottage Only Minutes from Downtown Keene, NH!, holiday rental in Winchester

Cozy Waterfront Cottage Only Minutes from Downtown Keene, NH!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Hilltop Home with Great Views, holiday rental in Winchester
Hilltop Home with Great Views, holiday rental in Winchester
Hilltop Home with Great Views, holiday rental in Winchester

Hilltop Home with Great Views

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy, pet-friendly one-bedroom apartment in Brattleboro, Vermont, holiday rental in Winchester
Cozy, pet-friendly one-bedroom apartment in Brattleboro, Vermont, holiday rental in Winchester
Cozy, pet-friendly one-bedroom apartment in Brattleboro, Vermont, holiday rental in Winchester

Cozy, pet-friendly one-bedroom apartment in Brattleboro, Vermont

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Large home for families or groups, holiday rental in Winchester
Large home for families or groups, holiday rental in Winchester
Large home for families or groups, holiday rental in Winchester

Large home for families or groups

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront New Englander Mt. Monadnock, holiday rental in Winchester
Waterfront New Englander Mt. Monadnock, holiday rental in Winchester
Waterfront New Englander Mt. Monadnock, holiday rental in Winchester

Waterfront New Englander Mt. Monadnock

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Penthouse - Steps to the Sandy Beach & clear water, holiday rental in Winchester
Penthouse - Steps to the Sandy Beach & clear water, holiday rental in Winchester
Penthouse - Steps to the Sandy Beach & clear water, holiday rental in Winchester

Penthouse - Steps to the Sandy Beach & clear water

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Serene Shelburne Studio Cabin w/Spring-Fed Pool!, holiday rental in Winchester
Serene Shelburne Studio Cabin w/Spring-Fed Pool!, holiday rental in Winchester
Serene Shelburne Studio Cabin w/Spring-Fed Pool!, holiday rental in Winchester

Serene Shelburne Studio Cabin w/Spring-Fed Pool!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Lake house getaway on pristine Spofford Lake, New Hampshire, holiday rental in Winchester
Lake house getaway on pristine Spofford Lake, New Hampshire, holiday rental in Winchester
Lake house getaway on pristine Spofford Lake, New Hampshire, holiday rental in Winchester

Lake house getaway on pristine Spofford Lake, New Hampshire

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Skywood - - Dublin, NH, holiday rental in Winchester
Skywood - - Dublin, NH, holiday rental in Winchester
Skywood - - Dublin, NH, holiday rental in Winchester

Skywood - - Dublin, NH

Holiday Rental House
8 bedrooms
6 bathrooms
Sleeps 13
Match: Sleeps
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PARADISE on EARTH! - Historic 4BR Farmhouse, holiday rental in Winchester
PARADISE on EARTH! - Historic 4BR Farmhouse, holiday rental in Winchester
PARADISE on EARTH! - Historic 4BR Farmhouse, holiday rental in Winchester

PARADISE on EARTH! - Historic 4BR Farmhouse

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Marlboro, Vermont Ski House - discount offered, holiday rental in Winchester
Marlboro, Vermont Ski House - discount offered, holiday rental in Winchester
Marlboro, Vermont Ski House - discount offered, holiday rental in Winchester

Marlboro, Vermont Ski House - discount offered

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Hemlock House at Aldworth Manor, holiday rental in Winchester
Hemlock House at Aldworth Manor, holiday rental in Winchester
Hemlock House at Aldworth Manor, holiday rental in Winchester

Hemlock House at Aldworth Manor

Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Victorian Lakefront Cottage With Spectacular Sunrise View Of Water, holiday rental in Winchester
Victorian Lakefront Cottage With Spectacular Sunrise View Of Water, holiday rental in Winchester
Victorian Lakefront Cottage With Spectacular Sunrise View Of Water, holiday rental in Winchester

Victorian Lakefront Cottage With Spectacular Sunrise View Of Water

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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A Healing Forest Space in the Heart of New England, holiday rental in Winchester
A Healing Forest Space in the Heart of New England, holiday rental in Winchester
A Healing Forest Space in the Heart of New England, holiday rental in Winchester

A Healing Forest Space in the Heart of New England

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Church sanctuary , holiday rental in Winchester
Church sanctuary , holiday rental in Winchester
Church sanctuary , holiday rental in Winchester

Church sanctuary

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lakeside Lodge with Rock Fireplace, holiday rental in Winchester
Lakeside Lodge with Rock Fireplace, holiday rental in Winchester
Lakeside Lodge with Rock Fireplace, holiday rental in Winchester

Lakeside Lodge with Rock Fireplace

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Fully Furnished/Pet Friendly!, holiday rental in Winchester
Fully Furnished/Pet Friendly!, holiday rental in Winchester
Fully Furnished/Pet Friendly!, holiday rental in Winchester

Fully Furnished/Pet Friendly!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Renovated Cottage w/spectacular mountain view, holiday rental in Winchester
Renovated Cottage w/spectacular mountain view, holiday rental in Winchester
Renovated Cottage w/spectacular mountain view, holiday rental in Winchester

Renovated Cottage w/spectacular mountain view

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Studio - Cozy Studio for 2 or 4!, holiday rental in Winchester
Studio - Cozy Studio for 2 or 4!, holiday rental in Winchester
Studio - Cozy Studio for 2 or 4!, holiday rental in Winchester

Studio - Cozy Studio for 2 or 4!

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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PoshHaus Court ST Colonial, holiday rental in Winchester
PoshHaus Court ST Colonial, holiday rental in Winchester
PoshHaus Court ST Colonial, holiday rental in Winchester

PoshHaus Court ST Colonial

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Jabulani Luxury Rural Stay, holiday rental in Winchester
Jabulani Luxury Rural Stay, holiday rental in Winchester
Jabulani Luxury Rural Stay, holiday rental in Winchester

Jabulani Luxury Rural Stay

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Bellows Cottage at The Inn at Valley Farms, holiday rental in Winchester
Bellows Cottage at The Inn at Valley Farms, holiday rental in Winchester
Bellows Cottage at The Inn at Valley Farms, holiday rental in Winchester

Bellows Cottage at The Inn at Valley Farms

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Picturesque Lakefront Retreat at Spofford Lake, Sleeps 10, holiday rental in Winchester
Picturesque Lakefront Retreat at Spofford Lake, Sleeps 10, holiday rental in Winchester
Picturesque Lakefront Retreat at Spofford Lake, Sleeps 10, holiday rental in Winchester

Picturesque Lakefront Retreat at Spofford Lake, Sleeps 10

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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