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Holiday homes in Pittsfield (Page 2)

Enjoy your stay and find the best Holiday homes in Pittsfield at affordable prices

Searching for a holiday home in Pittsfield (Massachusetts)? Explore a great selection of vacation homes in Pittsfield to find the one that best fits to your needs, starting from $101 per night. Holiday homes offer a relaxing escape, providing a cozy retreat for vacationers seeking a home away from home.

Holiday-homes in Pittsfield and region (30 miles)
The Lodge @ America’s Switzerland in North Adams, USA

The Lodge @ America’s Switzerland

Lodge in North Adams near Pittsfield, Massachusetts , 2360 Mohawk Trail
Boasting a garden, a terrace as well as a bar, The Lodge @ America’s Switzerland is situated in North Adams, within 40 km of Bennington Battle Monum...
  • Bar
  • Breakfast in the room

Fabulous 36 Reviews 8.7

from $192.50 Show details »

Restored 1800s Home Half Mile to Ski Resort! in Otis, USA

Restored 1800s Home Half Mile to Ski Res...

Holiday home in Otis near Pittsfield, Massachusetts
Set 26 km from Cranwell Spa & Golf Club and 30 km from Tanglewood in Otis, Restored 1800s Home Half Mile to Ski Resort! offers accommodation with a ki...
  • Parking

no reviews

from $284.29 Show details »

Waterfront Cottage 10 Min to Great Barrington! in New Marlborough, USA

Waterfront Cottage 10 Min to Great Barri...

Holiday home in New Marlborough near Pittsfield, Massachusetts
Waterfront Lake Buel Cottage 7 Mi to Monument Mtn is located in New Marlborough, 25 km from Cranwell Spa & Golf Club, 26 km from Tanglewood Musical Ce...
  • Parking
  • Internet facilities
  • Refrigerator
  • DVD player
  • Fan

Exceptional 1 Reviews 10.0

from $465.00 Show details »

Rustic Berkshires Cottage at Lake Buel with Kayaks! in New Marlborough, USA

Rustic Berkshires Cottage at Lake Buel w...

Holiday home in New Marlborough near Pittsfield, Massachusetts
Situated in New Marlborough, 21 km from Norman Rockwell Museum, 25 km from Cranwell Spa & Golf Club and 26 km from Tanglewood Musical Center, Rustic B...
  • Parking
  • Pets allowed

Superb 4 Reviews 9.3

from $262.67 Show details »

Florida Mountain Log Cabin in Florida, USA

Florida Mountain Log Cabin

Chalet in Florida near Pittsfield, Massachusetts , 1 Oleson Road
Featuring mountain views, Florida Mountain Log Cabin features accommodation with a terrace and a balcony, around 19 km from The Clark Art Institute.
  • Parking

Exceptional 4 Reviews 10.0

from $411.62 Show details »

Hoosac Range Retreat in Florida, USA

Hoosac Range Retreat

Holiday home in Florida near Pittsfield, Massachusetts , 137 Mohawk Trail
Set in Florida in the Massachusetts region, Hoosac Range Retreat has a balcony.
  • Parking
  • Family rooms

no reviews

from $142.64 Show details »

Cabin with 3 Acres, Tennis Courts By 4 Ski Mtns in Sandisfield, USA

Cabin with 3 Acres, Tennis Courts By 4 S...

Holiday home in Sandisfield near Pittsfield, Massachusetts
Situated in Sandisfield, 25 km from Cranwell Spa & Golf Club, 28 km from Norman Rockwell Museum and 29 km from Tanglewood, Cabin with 3 Acres, Tennis ...
  • Parking
  • Pets allowed
  • Internet facilities
  • Hairdryer
  • Refrigerator

Very good 1 Reviews 8.0

from $393.00 Show details »

Historic Huntington Home - Walk to Westfield River in Huntington, USA

Historic Huntington Home - Walk to Westf...

Holiday home in Huntington near Pittsfield, Massachusetts
Located in Huntington in the Massachusetts region, Historic Huntington Home - Walk to Westfield River has a patio and garden views.
  • Parking

Fabulous 1 Reviews 9.0

from $357.00 Show details »

Pet-Friendly Cabin with Fire Pit, BBQ and Great Deck! in Williamsburg, USA

Pet-Friendly Cabin with Fire Pit, BBQ an...

Holiday home in Williamsburg near Pittsfield, Massachusetts
Pet-Friendly Cabin with Fire Pit, BBQ and Great Deck! is situated in Williamsburg, 49 km from Eastern States Exposition Center, 49 km from The Big E, ...
  • Parking
  • Pets allowed

no reviews

from $380.00 Show details »

East Otis Vacation Rental with Private Deck and BBQ! in East Otis, USA

East Otis Vacation Rental with Private D...

Holiday home in East Otis near Pittsfield, Massachusetts
East Otis Romantic Cottage with Deck and BBQ! is situated in East Otis, 35 km from Cranwell Spa & Golf Club, 39 km from Tanglewood, as well as 39 km f...
  • Parking

Fabulous 1 Reviews 9.0

from $206.00 Show details »

East Otis Reservoir Cabin with Porch - Walk to Lake! in East Otis, USA

East Otis Reservoir Cabin with Porch - W...

Holiday home in East Otis near Pittsfield, Massachusetts
East Otis Reservoir Cabin with Porch - Walk to Lake! is set in East Otis, 35 km from Cranwell Spa & Golf Club, 39 km from Tanglewood, as well as 39 km...
  • Parking
  • Pets allowed

no reviews

from $153.00 Show details »

Waterview Home in the Berkshires Near Hiking in Sheffield, USA

Waterview Home in the Berkshires Near Hi...

Holiday home in Sheffield near Pittsfield, Massachusetts
Set 25 km from Norman Rockwell Museum, 31 km from Cranwell Spa & Golf Club and 32 km from Tanglewood Musical Center, Waterfront Sheffield Escape with ...
  • Parking

no reviews

from $340.67 Show details »

The Mill River Cabin with Fireplace and River View! in Mill River, USA

The Mill River Cabin with Fireplace and...

Holiday home in Mill River near Pittsfield, Massachusetts
The Mill River Cabin with Fireplace and River View! is situated in Mill River, 30 km from Norman Rockwell Museum, 35 km from Cranwell Spa & Golf Club,...
  • Parking
  • Pets allowed
  • Internet facilities
  • Hairdryer
  • Toilet

Superb 4 Reviews 9.5

from $244.33 Show details »

Number of Holiday homes in Pittsfield 38
Number of guest ratings 1907
Average price per night $460.92
Lowest price per night $101.00
Highest price per night $995.00

Most popular Holiday-homes in Pittsfield

The most popular Holiday-homes in Pittsfield based on average guest rating (Top 10).

Cheapest Holiday-homes in Pittsfield

The cheapest Holiday-homes in Pittsfield based on room rate per night (Top 10).

Most booked Holiday-homes in Pittsfield

The most booked Holiday-homes in Pittsfield based on popularity with guests (Top 10).

Holiday homes in Pittsfield (Massachusetts), comfortable and familiar

Staying in a holiday or vacation home in Pittsfield can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Pittsfield for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Pittsfield should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com