Hotels with Outdoor Pool and Parking near Ski Resorts in Pittsfield MA

Berkshire Inn

Motel in Pittsfield MA

7.3

Good

From $89

$

Info Categories

Motel near Ski Resorts

Motel with Parking

Motel with Swimming Pool

Outdoor Pool

17 more hotels nearby!

Huge 3 bdrm Designer House in Lenox 3.0 mi from Pittsfield

Vacation Home in Lenox MA

$

Info Categories

Vacation Home near Ski Resorts

Vacation Home with Parking

Vacation Home with Swimming Pool

Private Pool Outdoor Pool

Apple Tree Inn 6.6 mi from Pittsfield

Inn in Lenox MA

7.7

Good

From $146

$

Info Categories

Inn near Ski Resorts

Inn with Parking

Inn with Swimming Pool

Heated Pool Outdoor Pool

Walk to Tnglewd, Stckbrdg Bwl, Wheatleigh, HTd Pool, Hot Tub 6.9 mi from Pittsfield

Vacation Home in Lenox MA

8.8

Excellent

From $612

$

Info Categories

Vacation Home near Ski Resorts

Vacation Home with Parking

Vacation Home with Swimming Pool

Heated Pool Outdoor Pool

Wheatleigh 7.1 mi from Pittsfield

Hotel in Lenox MA

9.2

Excellent

From $912

$

Info Categories

Hotel near Ski Resorts

Hotel with Parking

EV charging stations

Hotel with Swimming Pool

Heated Pool Outdoor Pool

Seven Hills Inn 7.2 mi from Pittsfield

Inn in Lenox MA

7.2

Good

From $166

$

Info Categories

Inn near Ski Resorts

Inn with Parking

Inn with Swimming Pool

Heated Pool Outdoor Pool

Jiminy Peak Vacation Home 8.0 mi from Pittsfield

Vacation Home in Hancock MA

$

Info Categories

Vacation Home near Ski Resorts

Vacation Home with Parking

Vacation Home with Swimming Pool

Heated Pool Indoor Pool Outdoor Pool

Updated Jiminy Peak Condo w/ Patio & Pool Access! 8.2 mi from Pittsfield

Vacation Home in Hancock MA

$

Info Categories

Vacation Home near Ski Resorts

Vacation Home with Parking

Vacation Home with Swimming Pool

Outdoor Pool

American Inn Lee 8.5 mi from Pittsfield

Hotel in Lee MA

7.7

Good

$

Info Categories

Hotel near Ski Resorts

Hotel with Parking

Hotel with Swimming Pool

Outdoor Pool

Private Berkshire Escape Special April Pricing select your dates for discount Monthly Pricing 10.5 mi from Pittsfield

Vacation Home in Lee MA

$

Info Categories

Vacation Home near Ski Resorts

Vacation Home with Parking

Vacation Home with Swimming Pool

Outdoor Pool

Stockbridge Country Inn 11.6 mi from Pittsfield

Bed & Breakfast in Stockbridge MA

9.4

Excellent

From $336

$

Info Categories

Bed & Breakfast near Ski Resorts

Bed & Breakfast with Parking

Bed & Breakfast with Swimming Pool

Outdoor Pool

Clatter Hall 16.6 mi from Pittsfield

Vacation Home in Spencertown NY

$

Info Categories

Vacation Home near Ski Resorts

Vacation Home with Parking

Vacation Home with Swimming Pool

Outdoor Pool

Stay Berkshires 17.2 mi from Pittsfield

Hotel in Williamstown MA

6.6

Rated

From $179

$

Info Categories

Hotel near Ski Resorts

Hotel with Parking

Hotel with Swimming Pool

Outdoor Pool

Willows Motel 18.8 mi from Pittsfield

Motel in Williamstown MA

8.9

Excellent

From $99

$

Info Categories

Motel near Ski Resorts

Motel with Parking

Motel with Swimming Pool

Heated Pool Outdoor Pool

Maple Terrace Motel 18.9 mi from Pittsfield

Motel in Williamstown MA

9.2

Excellent

From $111

$

Info Categories

Motel near Ski Resorts

Motel with Parking

Motel with Swimming Pool

Heated Pool Outdoor Pool

Swiss Hütte Inn and Restaurant 21.4 mi from Pittsfield

Inn in Hillsdale NY

8.5

Very Good

$

Info Categories

Inn near Ski Resorts

Inn with Parking

Inn with Swimming Pool

Outdoor Pool

The Old Inn On The Green 21.9 mi from Pittsfield

Inn in New Marlborough MA

8.4

Very Good

From $308

$

Info Categories

Inn near Ski Resorts

Inn with Parking

Inn with Swimming Pool

Outdoor Pool

Summer and Fall in Sheffield with Monthly Special Pricing Available 23.5 mi from Pittsfield

Vacation Home in Sheffield MA

$

Info Categories

Vacation Home near Ski Resorts

Vacation Home with Parking

Vacation Home with Swimming Pool

Outdoor Pool