Vacation rentals in Tanglewood, MA

103 available vacation rental offers

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Best vacation rentals and Airbnb offers in Tanglewood, MA

Lenox in-law studio - Tanglewood, MA

Lenox in-law studio

Apartment, Tanglewood

Lenox in-law studio is a apartment in Tanglewood, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Lenox in-law studio

Lenox in-law studio is a apartment in Tanglewood, 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 $1,293.

From$185/night
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Cozy Stockbridge Cabin - Walk to Beach & Lake! - Tanglewood, MA

Cozy Stockbridge Cabin - Walk to Beach & Lake!

Holiday Home, Tanglewood

Cozy Stockbridge Cabin - Walk to Beach & Lake! is a holiday home in Tanglewood, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy Stockbridge Cabin - Walk to Beach & Lake!

Cozy Stockbridge Cabin - Walk to Beach & Lake! is a holiday home in Tanglewood, with easy beach access 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, free wifi, parking, paid parking, and non smoking::room.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,020.

From$206/night
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Downtown Gateway to the Berkshires. Walk to Everything. - Tanglewood, MA

Downtown Gateway to the Berkshires. Walk to Everything.

Apartment, Tanglewood

Downtown Gateway to the Berkshires. Walk to Everything. is a apartment in Tanglewood, 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 Tanglewood, 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 Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox) - Tanglewood, MA

Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox)

Condo, Tanglewood

Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox) is a condo in Tanglewood, with pet-friendly space and kitchen access. This stay gives travelers a…

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About Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox)

Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox) is a condo in Tanglewood, 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 $1,564.

From$223/night
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Vacation rentals with a pool in Tanglewood, MA

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

Villa with Access to Various Amenities - Tanglewood, MA

Villa with Access to Various Amenities

Villa, Tanglewood

Villa with Access to Various Amenities is a villa in Tanglewood, 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 Tanglewood, 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 $1,773.

From$253/night
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Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee - Tanglewood, MA

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

Apartment, Tanglewood

Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee is a apartment in Tanglewood, 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 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 Tanglewood, 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 - Tanglewood, MA

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

Apartment, Tanglewood

Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee is a apartment in Tanglewood, 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 Tanglewood, 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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Tranquil Lakeside Escape in the Berkshires - Tanglewood, MA

Tranquil Lakeside Escape in the Berkshires

Condo, Tanglewood

Tranquil Lakeside Escape in the Berkshires is a condo in Tanglewood, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Tranquil Lakeside Escape in the Berkshires

Tranquil Lakeside Escape in the Berkshires is a condo in Tanglewood, 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,367.

From$338/night
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Vacation rentals with parking in Tanglewood, MA

Find vacation rentals that make arriving by car easier.

Chic corporate apartment in wonderful Pittsfield with AC, WiFi - Tanglewood, MA

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Apartment, Tanglewood

Chic corporate apartment in wonderful Pittsfield with AC, WiFi is a apartment in Tanglewood, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Chic corporate apartment in wonderful Pittsfield with AC, WiFi is a apartment in Tanglewood, 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: parking, free parking, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,085.

From$155/night
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The Central Downtown Inn & Suites - Tanglewood, MA

The Central Downtown Inn & Suites

Guest House, Tanglewood

The Central Downtown Inn & Suites is a guest house in Tanglewood, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About The Central Downtown Inn & Suites

The Central Downtown Inn & Suites is a guest house in Tanglewood, 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 wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,405.

From$180/night
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NEW RENO - Historic Loft w/views of the Berkshires - Tanglewood, MA

NEW RENO - Historic Loft w/views of the Berkshires

Country House, Tanglewood

NEW RENO - Historic Loft w/views of the Berkshires is a country house in Tanglewood, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About NEW RENO - Historic Loft w/views of the Berkshires

NEW RENO - Historic Loft w/views of the Berkshires is a country house in Tanglewood, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,436.

From$205/night
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Shaker Mill Inn - Tanglewood, MA

Shaker Mill Inn

B & B, Tanglewood

Shaker Mill Inn is a b & b in Tanglewood, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Shaker Mill Inn

Shaker Mill Inn is a b & b in Tanglewood, 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 breakfast, parking, free parking, house keeping, and housekeeping.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,949.

From$254/night
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Pet-friendly vacation rentals in Tanglewood, MA

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

Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield - Tanglewood, MA

Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield

Apartment, Tanglewood

Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield is a apartment in Tanglewood, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a…

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About Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield

Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield is a apartment in Tanglewood, with pet-friendly space, 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: pet friendly, pets friendly, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,264.

From$181/night
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Shaker Mill Inn - Tanglewood, MA

Shaker Mill Inn

B & B, Tanglewood

Shaker Mill Inn is a b & b in Tanglewood, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

Read more

About Shaker Mill Inn

Shaker Mill Inn is a b & b in Tanglewood, 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 breakfast, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,205.

From$282/night
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Shaker Mill Inn - Tanglewood, MA

Shaker Mill Inn

B & B, Tanglewood

Shaker Mill Inn is a b & b in Tanglewood, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

Read more

About Shaker Mill Inn

Shaker Mill Inn is a b & b in Tanglewood, 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 breakfast, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,205.

From$282/night
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Whistler's Inn - Tanglewood, MA

Whistler's Inn

B & B, Tanglewood

Whistler's Inn is a b & b in Tanglewood, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

Read more

About Whistler's Inn

Whistler's Inn is a b & b in Tanglewood, 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 breakfast, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,279.

From$291/night
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Vacation rentals with a kitchen in Tanglewood, MA

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

2 bedroom Riverhouse in the Heart of the Berkshires! Summer & winter coziness! - Tanglewood, MA

2 bedroom Riverhouse in the Heart of the Berkshires! Summer & winter coziness!

Apartment, Tanglewood

2 bedroom Riverhouse in the Heart of the Berkshires! Summer & winter coziness! is a apartment in Tanglewood, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About 2 bedroom Riverhouse in the Heart of the Berkshires! Summer & winter coziness!

2 bedroom Riverhouse in the Heart of the Berkshires! Summer & winter coziness! is a apartment in Tanglewood, with parking, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,737.

From$248/night
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Charming 2-bedroom apartment in Lee with fitness room, WiFi - Tanglewood, MA

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

Apartment, Tanglewood

Charming 2-bedroom apartment in Lee with fitness room, WiFi is a apartment in Tanglewood, 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 Tanglewood, 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 - Tanglewood, MA

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

Apartment, Tanglewood

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

Read more

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 Tanglewood, 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 - Tanglewood, MA

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

Apartment, Tanglewood

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

Read more

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 Tanglewood, 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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Family-friendly vacation rentals in Tanglewood, MA

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

Berkshire Mountain Cottage: in the Heart of the Berkshires - Tanglewood, MA

Berkshire Mountain Cottage: in the Heart of the Berkshires

Cottage, Tanglewood

Berkshire Mountain Cottage: in the Heart of the Berkshires is a cottage in Tanglewood, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Berkshire Mountain Cottage: in the Heart of the Berkshires

Berkshire Mountain Cottage: in the Heart of the Berkshires is a cottage in Tanglewood, 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 $1,876.

From$268/night
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Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A/C, 4 bdrms, 2 bath - Tanglewood, MA

Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A/C, 4 bdrms, 2 bath

Holiday Home, Tanglewood

Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A/C, 4 bdrms, 2 bath is a holiday home in Tanglewood, with kitchen access and a quieter setting. This stay gives travelers a…

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About Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A/C, 4 bdrms, 2 bath

Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A/C, 4 bdrms, 2 bath is a holiday home in Tanglewood, with 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, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,045.

From$292/night
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Pine & Paddle | Pond Access • Kayaks - Tanglewood, MA

Pine & Paddle | Pond Access • Kayaks

Cottage, Tanglewood

Pine & Paddle · Pond Access · Kayaks is a cottage in Tanglewood, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Pine & Paddle | Pond Access • Kayaks

Pine & Paddle · Pond Access · Kayaks is a cottage in Tanglewood, 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 $2,323.

From$332/night
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Beachwood Cottage - Tanglewood, MA

Beachwood Cottage

Cottage, Tanglewood

Beachwood Cottage is a cottage in Tanglewood, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Beachwood Cottage

Beachwood Cottage is a cottage in Tanglewood, with pet-friendly space, easy beach 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,405.

From$344/night
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