Serene Berkshires Oasis with Pool and Sculpture Garden 12.0 km from Chester
Vacation Home in Otis MA
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Vacation Home with Parking

Vacation Home with Swimming Pool

Outdoor Pool  

Vacation Home with Free Wi-Fi

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Monterey Home with Hot Tub, Pool and Game Room! 14.2 km from Chester
Vacation Home in Monterey MA
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Vacation Home with Parking

Vacation Home with Swimming Pool

Outdoor Pool  

Vacation Home with Free Wi-Fi

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American Inn Lee 15.1 km from Chester
Hotel in Lee MA
7.7
Good
Info Categories
Hotel with Parking

Hotel with Swimming Pool

Outdoor Pool  

Hotel near Ski Resorts

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Country Charmer 15.5 km from Chester
Vacation Home in Lee MA
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Vacation Home with Parking

Vacation Home with Swimming Pool

Outdoor Pool  

Dog Friendly Vacation Home

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Vacation Home with Parking

Vacation Home with Swimming Pool

Outdoor Pool  

Vacation Home near Ski Resorts

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Seven Hills Inn 16.5 km from Chester
Inn in Lenox MA
7.2
Good
From $166
From $166
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Inn with Parking

Inn with Swimming Pool

Heated Pool    Outdoor Pool  

Luxury Inn

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Huge 3 bdrm Designer House in Lenox 16.5 km from Chester
Vacation Home in Lenox MA
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Vacation Home with Parking

Vacation Home with Swimming Pool

Private Pool    Outdoor Pool  

Vacation Home near Ski Resorts

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Lenox House with Screened Patio and Mountain View 16.7 km from Chester
Vacation Home in Lenox MA
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Vacation Home with Parking

Vacation Home with Swimming Pool

Outdoor Pool  

Dog Friendly Vacation Home

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Charming Lenox Home View of October Mountain 16.7 km from Chester
Vacation Home in Lenox MA
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Vacation Home with Parking

Vacation Home with Swimming Pool

Outdoor Pool  

Dog Friendly Vacation Home

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Rockspring by AvantStay Huge Berkshires Estate 16.9 km from Chester
Vacation Home in Stockbridge MA
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Vacation Home with Parking

Vacation Home with Swimming Pool

Indoor Pool    Outdoor Pool  

Vacation Home with Free Wi-Fi

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Wheatleigh 17.8 km from Chester
Hotel in Lenox MA
9.2
Excellent
From $912
From $912
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Hotel with Parking

EV charging stations  

Hotel with Swimming Pool

Heated Pool    Outdoor Pool  

Dog Friendly Hotel

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The Old Inn On The Green 17.8 km from Chester
Inn in New Marlborough MA
8.4
Very Good
From $308
From $308
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Inn with Parking

Inn with Swimming Pool

Outdoor Pool  

Inn with Rooms With Fireplace

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Walk to Tnglewd, Stckbrdg Bwl, Wheatleigh, HTd Pool, Hot Tub 17.9 km from Chester
Vacation Home in Lenox MA
8.8
Excellent
From $612
From $612
Info Categories
Vacation Home with Parking

Vacation Home with Swimming Pool

Heated Pool    Outdoor Pool  

Luxury Vacation Home

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Stockbridge Retreat with Pool and Hot Tub! 18.4 km from Chester
Vacation Home in Stockbridge MA
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Vacation Home with Parking

Vacation Home with Swimming Pool

Outdoor Pool  

Vacation Home with Free Wi-Fi

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Apple Tree Inn 18.6 km from Chester
Inn in Lenox MA
7.7
Good
From $146
From $146
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Inn with Parking

Inn with Swimming Pool

Heated Pool    Outdoor Pool  

Inn with Rooms With Fireplace

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Berkshire Inn 18.7 km from Chester
Motel in Pittsfield MA
7.3
Good
From $89
From $89
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Motel with Parking

Motel with Swimming Pool

Outdoor Pool  

Motel near Ski Resorts

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Muddy Brook Retreat 19.2 km from Chester
Vacation Home in Great Barrington MA
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Vacation Home with Parking

Vacation Home with Swimming Pool

Outdoor Pool  

Vacation Home with Free Wi-Fi

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Stockbridge Country Inn 19.5 km from Chester
Bed & Breakfast in Stockbridge MA
9.4
Excellent
From $336
From $336
Info Categories
Bed & Breakfast with Parking

Bed & Breakfast with Swimming Pool

Outdoor Pool  

Bed & Breakfast for Adults Only

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Wellspring by AvantStay Indoor Pool Views 20.1 km from Chester
Vacation Home in Richmond MA
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Vacation Home with Parking

Vacation Home with Swimming Pool

Outdoor Pool  

Vacation Home with Free Wi-Fi

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Quality Inn West Springfield 20.2 km from Chester
Hotel in West Springfield MA
6.7
Rated
From $91
From $91
Info Categories
Hotel with Parking

Hotel with Swimming Pool

Outdoor Pool  

Hotel Taking Steps Towards Sustainability

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*Additional taxes or fees may apply. Please check the final price before completing your booking.
Categories:
  •     Parking (28)
  •     Outdoor Pool (28)
  •     Pool (28)
  •     Heated Pool (5)
  •     Indoor Pool (2)
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  •     Honeymoon (1)
  •     EV charging stations (1)
  •     Sustainability Journey (1)
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  •     Boutique-Style (1)
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