Vacation rentals in Ashmere Lake, MA

35 available vacation rental offers

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Best vacation rentals and Airbnb offers in Ashmere Lake, MA

Hawley Home w/ Deck & Mtn Views: Swim, Ski & More! - Ashmere Lake, MA
10 ★ 1 reviews

Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!

Cottage, Ashmere Lake

Hawley Home w/ Deck & Mtn Views: Swim, Ski & More! is a cottage in Ashmere Lake, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

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About Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!

Hawley Home w/ Deck & Mtn Views: Swim, Ski & More! is a cottage in Ashmere Lake, with pet-friendly space, outdoor 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,960.

From$236/night
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Harbour House Inn - Ashmere Lake, MA
9.4 ★ 53 reviews

Harbour House Inn

B & B, Ashmere Lake

Harbour House Inn is a b & b in Ashmere Lake, 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 Harbour House Inn

Harbour House Inn is a b & b in Ashmere Lake, 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, free wifi, parking, free parking, and ac.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,822.

From$246/night
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Vacation Village in the Berkshires - Ashmere Lake, MA
8.8 ★ 2,389 reviews

Vacation Village in the Berkshires

Condo, Ashmere Lake

Vacation Village in the Berkshires is a condo in Ashmere Lake, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Vacation Village in the Berkshires

Vacation Village in the Berkshires is a condo in Ashmere Lake, 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: pool, free wifi, gym, and condominium.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $962.

From$113/night
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The Central Downtown Inn & Suites - Ashmere Lake, MA
8.6 ★ 368 reviews

The Central Downtown Inn & Suites

Guest House, Ashmere Lake

The Central Downtown Inn & Suites is a guest house in Ashmere Lake, 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 Ashmere Lake, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $973.

From$124/night
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Family-friendly vacation rentals in Ashmere Lake, MA

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

Hideaway Inn Lenox - Ashmere Lake, MA
8 ★ 3 reviews

Hideaway Inn Lenox

Guest House, Ashmere Lake

Hideaway Inn Lenox is a guest house in Ashmere Lake, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Hideaway Inn Lenox

Hideaway Inn Lenox is a guest house in Ashmere Lake, 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, kids friendly, kids friendly videos or books, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,127.

From$272/night
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Mountain Biking Hub: 5 Mi to Berkshire East! - Ashmere Lake, MA

Mountain Biking Hub: 5 Mi to Berkshire East!

Cottage, Ashmere Lake

Mountain Biking Hub: 5 Mi to Berkshire East! is a cottage in Ashmere Lake, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Mountain Biking Hub: 5 Mi to Berkshire East!

Mountain Biking Hub: 5 Mi to Berkshire East! is a cottage in Ashmere Lake, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,271.

From$272/night
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Hot Tub, Lake Views! All-season Hinsdale Haven - Ashmere Lake, MA

Hot Tub, Lake Views! All-season Hinsdale Haven

Cottage, Ashmere Lake

Hot Tub, Lake Views! All-season Hinsdale Haven is a cottage in Ashmere Lake, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Hot Tub, Lake Views! All-season Hinsdale Haven

Hot Tub, Lake Views! All-season Hinsdale Haven is a cottage in Ashmere Lake, 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, free wifi, kitchen, with kitchen, and tv.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,751.

From$410/night
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Picturesque Cottage With Sunroom on Ashmere Lake! - Ashmere Lake, MA

Picturesque Cottage With Sunroom on Ashmere Lake!

Cottage, Ashmere Lake

Picturesque Cottage With Sunroom on Ashmere Lake! is a cottage in Ashmere Lake, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Picturesque Cottage With Sunroom on Ashmere Lake!

Picturesque Cottage With Sunroom on Ashmere Lake! is a cottage in Ashmere Lake, 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, free wifi, kitchen, with kitchen, and washer.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,536.

From$426/night
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Pet-friendly vacation rentals in Ashmere Lake, MA

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

Massachusetts Vacation Rental w/ Deck & Grill - Ashmere Lake, MA

Massachusetts Vacation Rental w/ Deck & Grill

Holiday Home, Ashmere Lake

Massachusetts Vacation Rental w/ Deck & Grill is a holiday home in Ashmere Lake, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for…

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About Massachusetts Vacation Rental w/ Deck & Grill

Massachusetts Vacation Rental w/ Deck & Grill is a holiday home in Ashmere Lake, with pet-friendly space, outdoor 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, free wifi, pet friendly, pets friendly, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,902.

From$471/night
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Family-friendly Hancock Home: Walk to Slopes! - Ashmere Lake, MA

Family-friendly Hancock Home: Walk to Slopes!

Apartment, Ashmere Lake

Family-friendly Hancock Home: Walk to Slopes! is a apartment in Ashmere Lake, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for…

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About Family-friendly Hancock Home: Walk to Slopes!

Family-friendly Hancock Home: Walk to Slopes! is a apartment in Ashmere Lake, with pet-friendly space, pool 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 cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,680.

From$427/night
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Massachusetts Vacation Rental w/ Deck & Grill - Ashmere Lake, MA

Massachusetts Vacation Rental w/ Deck & Grill

Cottage, Ashmere Lake

Massachusetts Vacation Rental w/ Deck & Grill is a cottage in Ashmere Lake, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

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About Massachusetts Vacation Rental w/ Deck & Grill

Massachusetts Vacation Rental w/ Deck & Grill is a cottage in Ashmere Lake, with pet-friendly space, outdoor 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,052.

From$517/night
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Whistler's Inn - Ashmere Lake, MA

Whistler's Inn

B & B, Ashmere Lake

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

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About Whistler's Inn

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

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,836.

From$235/night
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Vacation rentals with a pool in Ashmere Lake, MA

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

Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak - Ashmere Lake, MA

Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak

Apartment, Ashmere Lake

Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak is a apartment in Ashmere Lake, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak

Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak is a apartment in Ashmere Lake, with pool 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, and gym.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,040.

From$136/night
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Relaxation Suite Jiminy-Must See Sleeps 4 - Ashmere Lake, MA

Relaxation Suite Jiminy-Must See Sleeps 4

Apartment, Ashmere Lake

Relaxation Suite Jiminy-Must See Sleeps 4 is a apartment in Ashmere Lake, with pool access, room for a group, and a quieter setting. This stay gives travelers a comfortable base for…

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About Relaxation Suite Jiminy-Must See Sleeps 4

Relaxation Suite Jiminy-Must See Sleeps 4 is a apartment in Ashmere Lake, with pool access, room for a group, 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, pool, free wifi, and gym.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,040.

From$136/night
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Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor - Ashmere Lake, MA

Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor

Apartment, Ashmere Lake

Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor is a apartment in Ashmere Lake, with pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor

Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor is a apartment in Ashmere Lake, 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, free wifi, and gym.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $996.

From$124/night
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Brook Farm Inn - Ashmere Lake, MA
9.4 ★ 164 reviews

Brook Farm Inn

B & B, Ashmere Lake

Brook Farm Inn is a b & b in Ashmere Lake, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Brook Farm Inn

Brook Farm Inn is a b & b in Ashmere Lake, with pool 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 breakfast, pool, free wifi, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,341.

From$420/night
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Vacation rentals with parking in Ashmere Lake, MA

Find vacation rentals that make arriving by car easier.

Mountain Biking Hub: 5 Mi to Berkshire East! - Ashmere Lake, MA

Mountain Biking Hub: 5 Mi to Berkshire East!

Holiday Home, Ashmere Lake

Mountain Biking Hub: 5 Mi to Berkshire East! is a holiday home in Ashmere Lake, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Mountain Biking Hub: 5 Mi to Berkshire East!

Mountain Biking Hub: 5 Mi to Berkshire East! is a holiday home in Ashmere Lake, 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, paid parking, and heating.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,188.

From$235/night
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Devonfield Inn B&B - Ashmere Lake, MA
10 ★ 138 reviews

Devonfield Inn B&B

B & B, Ashmere Lake

Devonfield Inn B&B is a b & b in Ashmere Lake, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Devonfield Inn B&B

Devonfield Inn B&B is a b & b in Ashmere Lake, with pool 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 breakfast, pool, free wifi, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,433.

From$439/night
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The Cornell Inn, Lenox & The Berkshires - Ashmere Lake, MA

The Cornell Inn, Lenox & The Berkshires

B & B, Ashmere Lake

The Cornell Inn, Lenox & The Berkshires is a b & b in Ashmere Lake, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires is a b & b in Ashmere Lake, 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, free wifi, for couples, wine or champagne, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,497.

From$310/night
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Eastgate Inn B&B - Ashmere Lake, MA

Eastgate Inn B&B

B & B, Ashmere Lake

Eastgate Inn B&B is a b & b in Ashmere Lake, 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 Eastgate Inn B&B

Eastgate Inn B&B is a b & b in Ashmere Lake, 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, free wifi, parking, paid parking, and fireplace.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,723.

From$215/night
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