4-Star Hotels, Inns, Vacation Homes, B&Bs with Swimming Pool in Pittsfield MA

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

Hotel in Pittsfield MA

7.3

Good

From $114

$

Info Categories

4-Star Hotel

Hotel with Swimming Pool

Heated Pool Indoor Pool

Hotel with Spa

Berkshire Mountain Lodge

Lodge in Pittsfield MA

8.4

Very Good

From $178

$

Info Categories

Lodge with Swimming Pool

Heated Pool Indoor Pool

4-Star Lodge

Luxury Lodge

14 more hotels nearby!

Hampton Terrace Inn 5.9 mi from Pittsfield

Hotel in Lenox MA

9.4

Excellent

From $320

$

Info Categories

Hotel with Swimming Pool

Heated Pool Outdoor Pool

4-Star Hotel

Luxury Hotel

Brook Farm Inn 6.1 mi from Pittsfield

Bed & Breakfast in Lenox MA

9.8

Excellent

From $180

$

Info Categories

Bed & Breakfast with Swimming Pool

Heated Pool Outdoor Pool

4-Star Bed & Breakfast

Accessible Bed & Breakfast

Seven Hills Inn 7.2 mi from Pittsfield

Inn in Lenox MA

7.2

Good

From $166

$

Info Categories

Inn with Swimming Pool

Heated Pool Outdoor Pool

4-Star Inn

Luxury Inn

Disney Magic at Jiminy Mountain 8.2 mi from Pittsfield

Hotel in Hancock MA

9.6

Excellent

$

Info Categories

Hotel with Swimming Pool

Outdoor Pool

4-Star Hotel

Hotel with Free Wi-Fi

Devonfield Inn 9.6 mi from Pittsfield

Bed & Breakfast in Lee MA

9.2

Excellent

From $311

$

Info Categories

Bed & Breakfast with Swimming Pool

Heated Pool Outdoor Pool

4-Star Bed & Breakfast

Bed & Breakfast with Rooms With Fireplace

The Springs Motel 10.6 mi from Pittsfield

Hotel in New Ashford MA

8.2

Very Good

$

Info Categories

Hotel with Swimming Pool

4-Star Hotel

Hotel near Ski Resorts

The Red Lion Inn 11.2 mi from Pittsfield

Hotel in Stockbridge MA

8.0

Very Good

From $156

$

Info Categories

4-Star Hotel

Hotel with Swimming Pool

Outdoor Pool

Historic Hotel

Stockbridge Country Inn 11.6 mi from Pittsfield

Bed & Breakfast in Stockbridge MA

9.4

Excellent

From $336

$

Info Categories

Bed & Breakfast with Swimming Pool

Outdoor Pool

4-Star Bed & Breakfast

Bed & Breakfast for Adults Only

Magical Country Retreat in the Berkshires 15.2 mi from Pittsfield

Vacation Home in Great Barrington MA

$

Info Categories

Vacation Home with Swimming Pool

Outdoor Pool

4-Star Vacation Home

Family Friendly Vacation Home

The 1896 House Country Inn - Brookside & Pondside 17.7 mi from Pittsfield

Inn in Williamstown MA

6.3

Rated

From $111

$

Info Categories

Inn with Swimming Pool

Heated Pool

4-Star Inn

Inn with Rooms With Jacuzzi / Hot-tub

Berkshire Vacation Rentals: Mountain View Estate Sleeps 18 18.4 mi from Pittsfield

Vacation Home in North Egremont MA

$

Info Categories

Vacation Home with Swimming Pool

Outdoor Pool

4-Star Vacation Home

Dog Friendly Vacation Home

Berkshire Vacation Rentals: Private Estate Heated YEARROUND Outdoor Pool 18.8 mi from Pittsfield

Vacation Home in North Egremont MA

$

Info Categories

Vacation Home with Swimming Pool

Outdoor Pool

4-Star Vacation Home

Dog Friendly Vacation Home

The Porches Inn at Mass MoCA 19.7 mi from Pittsfield

Inn in North Adams MA

8.7

Very Good

From $226

$

Info Categories

Inn with Swimming Pool

Heated Pool Outdoor Pool

4-Star Inn

Inn with Parking

EV charging stations

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 with Swimming Pool

Outdoor Pool

4-Star Inn

Inn with Rooms With Fireplace

4-Star Hotels with Swimming Pool in Pittsfield MA