Cozy Becket Cottage Escape with Lake Access! 5.7 km from Chester
Vacation Home in Becket MA
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Vacation Home with Swimming Pool

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Rustic-Chic Home with Decks Pool and Lake Access 9.7 km from Chester
Vacation Home in Otis MA
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Vacation Home with Swimming Pool

Vacation Home with Parking

Vacation Home with Free Wi-Fi

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Lakefront Westhampton Cabin with Beach and Kayaks! 10.4 km from Chester
Vacation Home in Westhampton MA
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Vacation Home with Swimming Pool

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Vacation Home with Free Wi-Fi

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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 Swimming Pool

Outdoor Pool  

Vacation Home with Parking

Vacation Home with Free Wi-Fi

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Monterey Haven Less Than half Mi to Lake Garfield with Kayaks 13.4 km from Chester
Vacation Home in Monterey MA
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Vacation Home with Swimming Pool

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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 Swimming Pool

Outdoor Pool  

Vacation Home with Parking

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
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Hotel with Swimming Pool

Outdoor Pool  

Hotel with Parking

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 Swimming Pool

Outdoor Pool  

Vacation Home with Parking

Dog Friendly Vacation Home

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Info Categories
Vacation Home with Swimming Pool

Outdoor Pool  

Vacation Home with Parking

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 Swimming Pool

Heated Pool    Outdoor Pool  

Inn with Parking

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 Swimming Pool

Private Pool    Outdoor Pool  

Vacation Home with Parking

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 Swimming Pool

Outdoor Pool  

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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 Swimming Pool

Outdoor Pool  

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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 Swimming Pool

Indoor Pool    Outdoor Pool  

Vacation Home with Parking

Vacation Home with Free Wi-Fi

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Quality Inn & Suites Northampton - Amherst 17.4 km from Chester
Hotel in Northampton MA
6.0
Rated
From $138
From $138
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Hotel with Swimming Pool

Heated Pool    Indoor Pool  

Hotel with Parking

Hotel Taking Steps Towards Sustainability

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Berkshire Mountain Lodge 17.6 km from Chester
Lodge in Pittsfield MA
8.4
Very Good
From $178
From $178
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Lodge with Swimming Pool

Heated Pool    Indoor Pool  

Lodge with Parking

Luxury Lodge

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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 Swimming Pool

Heated Pool    Outdoor Pool  

Hotel with Parking

EV charging stations  

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 Swimming Pool

Outdoor Pool  

Inn with Parking

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
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Vacation Home with Swimming Pool

Heated Pool    Outdoor Pool  

Vacation Home with Parking

Luxury Vacation Home

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Fairfield Inn & Suites by Marriott Springfield Holyoke 18.2 km from Chester
Hotel in Holyoke MA
9.0
Excellent
From $151
From $151
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Hotel with Swimming Pool

Indoor Pool  

Hotel with Parking

Hotel Taking Steps Towards Sustainability

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*Additional taxes or fees may apply. Please check the final price before completing your booking.
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