Vacation rentals in The Berkshires, MA

66 available vacation rental offers

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Best Vacation rentals and Airbnb offers in The Berkshires, MA

East Otis Reservoir Cabin w/ Porch - Walk to Lake! - The Berkshires, MA

East Otis Reservoir Cabin w/ Porch - Walk to Lake!

Holiday Home, The Berkshires

East Otis Reservoir Cabin w/ Porch - Walk to Lake! is a holiday home in The Berkshires, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the…

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About East Otis Reservoir Cabin w/ Porch - Walk to Lake!

East Otis Reservoir Cabin w/ Porch - Walk to Lake! is a holiday home in The Berkshires, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,492.

From$153/night
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East Otis Reservoir Cabin w/ Porch - Walk to Lake! - The Berkshires, MA

East Otis Reservoir Cabin w/ Porch - Walk to Lake!

Cottage, The Berkshires

East Otis Reservoir Cabin w/ Porch - Walk to Lake! is a cottage in The Berkshires, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About East Otis Reservoir Cabin w/ Porch - Walk to Lake!

East Otis Reservoir Cabin w/ Porch - Walk to Lake! is a cottage in The Berkshires, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,552.

From$181/night
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Cozy Becket Cottage Escape w/ Lake Access! - The Berkshires, MA

Cozy Becket Cottage Escape w/ Lake Access!

Cottage, The Berkshires

Cozy Becket Cottage Escape w/ Lake Access! is a cottage in The Berkshires, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cozy Becket Cottage Escape w/ Lake Access!

Cozy Becket Cottage Escape w/ Lake Access! is a cottage in The Berkshires, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,392.

From$199/night
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East Otis Reservoir Cabin w/ Porch - Walk to Lake! - The Berkshires, MA

East Otis Reservoir Cabin w/ Porch - Walk to Lake!

Cabin, The Berkshires

East Otis Reservoir Cabin w/ Porch - Walk to Lake! is a cabin in The Berkshires, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About East Otis Reservoir Cabin w/ Porch - Walk to Lake!

East Otis Reservoir Cabin w/ Porch - Walk to Lake! is a cabin in The Berkshires, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,407.

From$201/night
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Browse Vacation Rentals with a Pool in The Berkshires, MA

Add a pool to the search when you want an easy place to cool off between outings.

Villa with Access to Various Amenities - The Berkshires, MA

Villa with Access to Various Amenities

Villa, The Berkshires

Villa with Access to Various Amenities is a villa in The Berkshires, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Villa with Access to Various Amenities

Villa with Access to Various Amenities is a villa in The Berkshires, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,877.

From$268/night
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Charming 2-bedroom apartment in Lee with fitness room, WiFi - The Berkshires, MA

Charming 2-bedroom apartment in Lee with fitness room, WiFi

Apartment, The Berkshires

Charming 2-bedroom apartment in Lee with fitness room, WiFi is a apartment in The Berkshires, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Charming 2-bedroom apartment in Lee with fitness room, WiFi

Charming 2-bedroom apartment in Lee with fitness room, WiFi is a apartment in The Berkshires, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,040.

From$291/night
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Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee - The Berkshires, MA

Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee

Apartment, The Berkshires

Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee is a apartment in The Berkshires, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee

Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee is a apartment in The Berkshires, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,040.

From$291/night
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Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee - The Berkshires, MA

Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee

Apartment, The Berkshires

Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee is a apartment in The Berkshires, with pool access, kitchen access, and room for a group. This stay gives travelers a…

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About Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee

Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee is a apartment in The Berkshires, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,040.

From$291/night
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Best The Berkshires, MA vacation rentals with parking

Find vacation rentals that make arriving by car easier.

The Docent`s House - Honoring a Legacy - The Berkshires, MA

The Docent`s House - Honoring a Legacy

Holiday Home, The Berkshires

The Docent`s House - Honoring a Legacy is a holiday home in The Berkshires, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About The Docent`s House - Honoring a Legacy

The Docent`s House - Honoring a Legacy is a holiday home in The Berkshires, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,065.

From$295/night
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Lakes & Leisure! Spacious Berkshire Getaway - The Berkshires, MA

Lakes & Leisure! Spacious Berkshire Getaway

Holiday Home, The Berkshires

Lakes & Leisure! Spacious Berkshire Getaway is a holiday home in The Berkshires, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Lakes & Leisure! Spacious Berkshire Getaway

Lakes & Leisure! Spacious Berkshire Getaway is a holiday home in The Berkshires, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,079.

From$440/night
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Hilltop Escape with Views & Hot Tub - The Berkshires, MA

Hilltop Escape with Views & Hot Tub

Holiday Home, The Berkshires

Hilltop Escape with Views & Hot Tub is a holiday home in The Berkshires, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Hilltop Escape with Views & Hot Tub

Hilltop Escape with Views & Hot Tub is a holiday home in The Berkshires, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,113.

From$445/night
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Locust Tree Bed and Breakfast LLC - The Berkshires, MA

Locust Tree Bed and Breakfast LLC

B & B, The Berkshires

Locust Tree Bed and Breakfast LLC is a b & b in The Berkshires, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC is a b & b in The Berkshires, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free breakfast, parking, free parking, and breakfast::free.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $845.

From$105/night
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Best Pet-Friendly Vacation Rentals in The Berkshires, MA

Bring your pet along with stays that welcome four-legged travelers.

Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts - The Berkshires, MA

Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts

Holiday Home, The Berkshires

Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts is a holiday home in The Berkshires, with pet-friendly space. This stay gives travelers a comfortable base for…

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About Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts

Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts is a holiday home in The Berkshires, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $600.

From$86/night
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Misty Pines Cabin | Wood Stove • Sauna - The Berkshires, MA

Misty Pines Cabin | Wood Stove • Sauna

Cabin, The Berkshires

Misty Pines Cabin · Wood Stove · Sauna is a cabin in The Berkshires, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Misty Pines Cabin | Wood Stove • Sauna

Misty Pines Cabin · Wood Stove · Sauna is a cabin in The Berkshires, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,470.

From$353/night
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Log Cabin w/ fire pit, close to Ski Catamount, Butternut Ski, Great Barrington - The Berkshires, MA

Log Cabin w/ fire pit, close to Ski Catamount, Butternut Ski, Great Barrington

Holiday Home, The Berkshires

Log Cabin w/ fire pit, close to Ski Catamount, Butternut Ski, Great Barrington is a holiday home in The Berkshires, with parking and kitchen access. This stay gives travelers a comfortable…

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About Log Cabin w/ fire pit, close to Ski Catamount, Butternut Ski, Great Barrington

Log Cabin w/ fire pit, close to Ski Catamount, Butternut Ski, Great Barrington is a holiday home in The Berkshires, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,835.

From$405/night
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LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE - The Berkshires, MA

LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE

Cottage, The Berkshires

LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE is a cottage in The Berkshires, with pet-friendly space and easy beach access. This stay gives travelers a comfortable base for exploring the…

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About LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE

LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE is a cottage in The Berkshires, with pet-friendly space and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,082.

From$726/night
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Best The Berkshires, MA vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

Downtown Gateway to the Berkshires. Walk to Everything. - The Berkshires, MA

Downtown Gateway to the Berkshires. Walk to Everything.

Apartment, The Berkshires

Downtown Gateway to the Berkshires. Walk to Everything. is a apartment in The Berkshires, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Downtown Gateway to the Berkshires. Walk to Everything.

Downtown Gateway to the Berkshires. Walk to Everything. is a apartment in The Berkshires, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,491.

From$213/night
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Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee - The Berkshires, MA

Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee

Apartment, The Berkshires

Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee is a apartment in The Berkshires, with pool access, kitchen access, and room for a group. This stay gives travelers…

Read more

About Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee

Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee is a apartment in The Berkshires, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,040.

From$291/night
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Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee - The Berkshires, MA

Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee

Apartment, The Berkshires

Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee is a apartment in The Berkshires, with pool access, kitchen access, and room for a group. This stay gives travelers a…

Read more

About Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee

Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee is a apartment in The Berkshires, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,040.

From$291/night
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Spacious Villa with Access to Various Amenities! - The Berkshires, MA

Spacious Villa with Access to Various Amenities!

Villa, The Berkshires

Spacious Villa with Access to Various Amenities! is a villa in The Berkshires, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Spacious Villa with Access to Various Amenities!

Spacious Villa with Access to Various Amenities! is a villa in The Berkshires, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,421.

From$346/night
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Our Favorite Family-Friendly Vacation Rentals in The Berkshires, MA

Plan a trip with stays that give families more room to spread out.

Relax And Enjoy A Fun Getaway At The Bacchus Cottage! - The Berkshires, MA

Relax And Enjoy A Fun Getaway At The Bacchus Cottage!

Cottage, The Berkshires

Relax And Enjoy A Fun Getaway At The Bacchus Cottage! is a cottage in The Berkshires, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Relax And Enjoy A Fun Getaway At The Bacchus Cottage!

Relax And Enjoy A Fun Getaway At The Bacchus Cottage! is a cottage in The Berkshires, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,145.

From$164/night
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Lovely Lakefront Cottage, Peaceful Setting, Hiking And More - The Berkshires, MA

Lovely Lakefront Cottage, Peaceful Setting, Hiking And More

Holiday Home, The Berkshires

Lovely Lakefront Cottage, Peaceful Setting, Hiking And More is a holiday home in The Berkshires, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Lovely Lakefront Cottage, Peaceful Setting, Hiking And More

Lovely Lakefront Cottage, Peaceful Setting, Hiking And More is a holiday home in The Berkshires, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,163.

From$309/night
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Spacious Comfortable Charming Family Farmhouse Great Location - The Berkshires, MA

Spacious Comfortable Charming Family Farmhouse Great Location

Country House, The Berkshires

Spacious Comfortable Charming Family Farmhouse Great Location is a country house in The Berkshires, with kitchen access and room for a group. This stay gives travelers a comfortable base…

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About Spacious Comfortable Charming Family Farmhouse Great Location

Spacious Comfortable Charming Family Farmhouse Great Location is a country house in The Berkshires, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,737.

From$391/night
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Enchanted Cottage On Babbling Brook - The Berkshires, MA

Enchanted Cottage On Babbling Brook

Cottage, The Berkshires

Enchanted Cottage On Babbling Brook is a cottage in The Berkshires, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Enchanted Cottage On Babbling Brook

Enchanted Cottage On Babbling Brook is a cottage in The Berkshires, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,080.

From$583/night
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