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

3-Star Vacation Home

Vacation Home with Free Wi-Fi

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

3-Star Vacation Home

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
Info Categories
Vacation Home with Swimming Pool

3-Star Vacation Home

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
Info Categories
Vacation Home with Swimming Pool

3-Star Vacation Home

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
Info Categories
Vacation Home with Swimming Pool

Outdoor Pool  

3-Star Vacation Home

Vacation Home with Free Wi-Fi

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Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires an IHG Hotel 15.9 km from Chester
Hotel in South Lee MA
8.4
Very Good
From $124
From $124
Info Categories
Hotel with Swimming Pool

Heated Pool    Indoor Pool    Outdoor Pool  

3-Star Hotel

Hotel 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
Info Categories
Vacation Home with Swimming Pool

Outdoor Pool  

3-Star Vacation Home

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
Info Categories
Vacation Home with Swimming Pool

Outdoor Pool  

3-Star Vacation Home

Dog Friendly Vacation Home

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Conroy's B&B 16.9 km from Chester
Bed & Breakfast in Stockbridge MA
8.7
Very Good
From $57
From $57
Info Categories
Bed & Breakfast with Swimming Pool

Outdoor Pool  

3-Star Bed & Breakfast

Bed & Breakfast near Ski Resorts

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Hampton Inn & Suites Berkshires-Lenox 17.4 km from Chester
Hotel in Lenox MA
8.7
Very Good
From $139
From $139
Info Categories
Hotel with Swimming Pool

Indoor Pool  

3-Star Hotel

Hotel near Ski Resorts

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The Yankee, Trademark Collection by Wyndham 17.5 km from Chester
Hotel in Lenox MA
8.3
Very Good
From $103
From $103
Info Categories
Hotel with Swimming Pool

Heated Pool    Indoor Pool  

3-Star Hotel

Family Friendly Hotel

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Hilton Garden Inn Lenox Pittsfield 17.5 km from Chester
Hotel in Pittsfield MA
8.6
Very Good
From $174
From $174
Info Categories
Hotel with Swimming Pool

Indoor Pool  

3-Star Hotel

Hotel near Ski Resorts

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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
Info Categories
Hotel with Swimming Pool

Indoor Pool  

3-Star Hotel

Hotel Taking Steps Towards Sustainability

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Homewood Suites by Hilton Holyoke-Springfield/North 18.3 km from Chester
Hotel in Holyoke MA
8.5
Very Good
From $169
From $169
Info Categories
Hotel with Swimming Pool

Heated Pool    Indoor Pool  

3-Star Hotel

Hotel Taking Steps Towards Sustainability

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D. Hotel Suites & Spa 18.4 km from Chester
Hotel in Holyoke MA
8.8
Excellent
From $155
From $155
Info Categories
Hotel with Swimming Pool

Heated Pool    Indoor Pool  

3-Star Hotel

Hotel with Spa

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

Outdoor Pool  

3-Star Vacation Home

Vacation Home with Free Wi-Fi

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Hampton Inn Hadley-Amherst Area 18.6 km from Chester
Hotel in Hadley MA
8.4
Very Good
From $165
From $165
Info Categories
Hotel with Swimming Pool

Heated Pool    Indoor Pool  

3-Star Hotel

Hotel Taking Steps Towards Sustainability

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Thornewood Inn 19.9 km from Chester
Inn in Great Barrington MA
8.1
Very Good
From $280
From $280
Info Categories
Inn with Swimming Pool

Outdoor Pool  

3-Star Inn

Inn near Ski Resorts

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Knights Inn Hadley 20.1 km from Chester
Motel in Hadley MA
8.3
Very Good
From $125
From $125
Info Categories
Motel with Swimming Pool

Outdoor Pool  

3-Star Motel

Dog Friendly Motel

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Residence Inn by Marriott West Springfield 20.2 km from Chester
Hotel in West Springfield MA
8.1
Very Good
From $141
From $141
Info Categories
Hotel with Swimming Pool

Heated Pool    Indoor Pool  

3-Star Hotel

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:
  •     3 Star (35)
  •     Pool (35)
  •     Indoor Pool (18)
  •     Heated Pool (11)
  •     Outdoor Pool (11)
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  •     Parking (19)
  •     Accessible (19)
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  •     Free Wi-Fi (15)
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  •     Family (13)
  •     Sustainability Journey (12)
  •     Honeymoon (12)
  •     Ski (7)
  •     Golf (3)
  •     Rooms with Fireplace (2)
  •     Small (2)
  •     Tennis (2)
  •     EV charging stations (1)
  •     Dogs Stay Free (1)
  •     Spa (1)
  •     Rooms with Jacuzzi / Hot-Tub (1)
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