Pittsfield Holiday Homes from €114: Search Top House Rentals

Pittsfield Holiday Homes
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Our top choices for Pittsfield holiday homes

3 bedrooms, desk, iron/ironing board, WiFi

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

7.8 out of 10, Good, (7 reviews)

7.8/10

Good

(7 reviews)

"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."

Liz V.

The price is €415

€415

includes taxes & fees

22 Apr - 23 Apr

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Hancock Village Inn Near Jiminy Peak

Hancock

10.0 out of 10, Exceptional, (19 reviews)

10/10

Exceptional

(19 reviews)

"Amazing Inn. Cozy and everything we needed. "

Price F.

The price is €980

€980

includes taxes & fees

21 Apr - 22 Apr

Hancock Village Inn Near Jiminy Peak

2 bedrooms, desk, iron/ironing board, travel cot

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

9.8 out of 10, Exceptional, (14 reviews)

9.8/10

Exceptional

(14 reviews)

"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"

Matthew F.

The price is €330

€330

includes taxes & fees

19 Apr - 20 Apr

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"We loved it! Lots of local hiking trails and a wonderful relaxing place."

Sharon K.

The price is €320

€320

includes taxes & fees

28 Apr - 29 Apr

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

4 bedrooms, desk, iron/ironing board, WiFi

North Getaway Cottage

Williamstown

9.2 out of 10, Wonderful, (24 reviews)

9.2/10

Wonderful

(24 reviews)

"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"

Carole S.

The price is €374

€374

includes taxes & fees

20 Apr - 21 Apr

North Getaway Cottage

Florida Mountain Log Cabin

Florida

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Place was super clean. Beds were comfortable. Location was great."

Tristan e.

The price is €290

€290

includes taxes & fees

19 Apr - 20 Apr

Florida Mountain Log Cabin

2 bedrooms, iron/ironing board, WiFi, bed sheets

Home in Great Barrington

Great Barrington

9.8 out of 10, Exceptional, (29 reviews)

9.8/10

Exceptional

(29 reviews)

"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "

maureen k.

The price is €273

€273

includes taxes & fees

28 Apr - 29 Apr

Home in Great Barrington

Smart TV, fireplace, books, music library

Cozy Riverside Berkshires Retreat

Great Barrington

9.2 out of 10, Wonderful, (14 reviews)

9.2/10

Wonderful

(14 reviews)

"Close to a great bakery and near to a farm market and shopping mall. "

Cristine C.

The price is €266

€266

includes taxes & fees

21 Apr - 22 Apr

Cozy Riverside Berkshires Retreat

Cozy Home in Pownal VT

Pownal

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."

Jess M.

The price is €164

€164

includes taxes & fees

19 Apr - 20 Apr

Cozy Home in Pownal VT

Artists’ Hideaway in Old Chatham

Old Chatham

The price is €433

€433

includes taxes & fees

5 May - 6 May

Artists’ Hideaway in Old Chatham

Fridge, microwave, coffee/tea maker, toaster

Treat yourself at the stunning June Farms Wellness Huts!

West Sand Lake

10.0 out of 10, Exceptional, (8 reviews)

10/10

Exceptional

(8 reviews)

"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."

SteveS

The price is €405

€405

includes taxes & fees

23 Apr - 24 Apr

Treat yourself at the stunning June Farms Wellness Huts!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge

10.0 out of 10, Exceptional, (36 reviews)

10/10

Exceptional

(36 reviews)

"Charming house in a wonderful setting in the Berkshires. "

Mark Cristen J.

The price is €608

€608

includes taxes & fees

10 May - 11 May

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

3 bedrooms, iron/ironing board, free WiFi, bed sheets

Near Tanglewood: Historic Summer Retreat

New Lebanon

9.4 out of 10, Exceptional, (26 reviews)

9.4/10

Exceptional

(26 reviews)

"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."

Paul S.

The price is €351

€351

includes taxes & fees

12 May - 13 May

Near Tanglewood: Historic Summer Retreat

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Lebanon Springs

9.0 out of 10, Wonderful, (21 reviews)

9.0/10

Wonderful

(21 reviews)

"Comfy beds, clean, great big deck with a view. "

Corinne T.

The price is €406

€406

includes taxes & fees

20 Apr - 21 Apr

Historic Berkshires Home Near Tanglewood, Trails & Wineries

The Greylock Cabin

Florida

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"the hosts were great very helpful and pleasant"

Ron L.

The price is €321

€321

includes taxes & fees

17 May - 18 May

The Greylock Cabin

Comfortable Berkshires retreat on mtn resort, SISO

Hancock

8.8 out of 10, Excellent, (8 reviews)

8.8/10

Excellent

(8 reviews)

"Kind and responsive host."

Javier

The price is €453

€453

includes taxes & fees

18 Apr - 19 Apr

Comfortable Berkshires retreat on mtn resort, SISO

Treetop Hideaway in Tyringham

Monterey

9.2 out of 10, Wonderful, (11 reviews)

9.2/10

Wonderful

(11 reviews)

"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"

Sarah B.

The price is €470

€470

includes taxes & fees

21 Apr - 22 Apr

Treetop Hideaway in Tyringham

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"

Roberta

The price is €1,126

€1,126

includes taxes & fees

23 Apr - 24 Apr

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"Great experience! Only there for one night because our son had a wrestling tournament. Wish we would have had more time at property. "

Rochelle F.

The price is €266

€266

includes taxes & fees

22 Apr - 23 Apr

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

The price is €114

€114

includes taxes & fees

12 May - 13 May

Real Estate: Therapy - Lake, Laundry, Love it

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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