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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 440 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

Safe Peaceful Quite Bright Gorgeous Accessibility
Miscellaneous

Safe Peaceful Quite Bright Gorgeous Accessibility

The price is AED 404
AED 956 total
includes taxes & fees
14 May - 15 May
Safe Peaceful Quite Bright Gorgeous Accessibility
Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock
Outdoor dining

Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock

9.6 out of 10, Exceptional, (20)
"Very peaceful spot, we had everything we needed."
Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock
Lake Access, Mtn Views, Game Room, Hot Tub & More!
Miscellaneous

Lake Access, Mtn Views, Game Room, Hot Tub & More!

Lake Access, Mtn Views, Game Room, Hot Tub & More!
Updated Cape home with WiFi, W/D, full kitchen & clawfoot tub
Fridge, microwave, oven, stovetop

Updated Cape home with WiFi, W/D, full kitchen & clawfoot tub

9.8 out of 10, Exceptional, (31)
"We were in town for a family event and the property and location was just right for 5 of us."
Updated Cape home with WiFi, W/D, full kitchen & clawfoot tub
Six-Bedroom Family Retreat Near Portsmouth
Aerial view

Six-Bedroom Family Retreat Near Portsmouth

Six-Bedroom Family Retreat Near Portsmouth
Barn Off the beaten path yet close to everything.
1 bedroom, free WiFi, bed sheets

Barn Off the beaten path yet close to everything.

10.0 out of 10, Exceptional, (17)
"Clean, cute and cozy."
Barn Off the beaten path yet close to everything.
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
Indoor pool

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

10.0 out of 10, Exceptional, (168)
"House was great! Very short drive to gunstock mountain for skiing. The pool and hot tub was a big hit and a great way to spend some time post skiing.Highly recommended "
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock
Terrace/patio

Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock

9.8 out of 10, Exceptional, (97)
"Such a cozy cabin. Loved our stay."
Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock
Stargazer's retreat with hot tub & decks - near Ellacoya State Beach
Outdoor spa tub

Stargazer's retreat with hot tub & decks - near Ellacoya State Beach

8.2 out of 10, Very Good, (29)
"We had a great stay at this property. It was very conveniently located near Gunstock Ski Resort. The hot tub was perfect after a long day skiing and tubing. The home was clean and well-furnished."
Stargazer's retreat with hot tub & decks - near Ellacoya State Beach
Charming and spacious lakefront home w/hot tub and pool table!
Exterior

Charming and spacious lakefront home w/hot tub and pool table!

10.0 out of 10, Exceptional, (49)
"This was our 3rd stay here and had a great time as always. Great hosts and great house with everything you could ask for in a vacation home."
Charming and spacious lakefront home w/hot tub and pool table!
Waterfront with Kayaks, Pool Table, Fire Pit, and Pergola. Downtown area
Terrace/patio

Waterfront with Kayaks, Pool Table, Fire Pit, and Pergola. Downtown area

9.8 out of 10, Exceptional, (29)
"We enjoyed our stay. The view of the river was very nice. The host was very attentive so we had everything we needed and more. It’s a property in the heart of the city, so we walked to local places which was a bonus."
The price is AED 547
AED 1,120 total
includes taxes & fees
14 May - 15 May
Waterfront with Kayaks, Pool Table, Fire Pit, and Pergola. Downtown area
Reuben Dimond House, Renovated Historic Farmhouse in the Capital, Concord, NH.
Miscellaneous

Reuben Dimond House, Renovated Historic Farmhouse in the Capital, Concord, NH.

10.0 out of 10, Exceptional, (64)
"Our second 2 week vacation at Reuben Dimond house.A cosy comfortable home away from home with everything we could want and more.Many thanks Lynn for all your care and attention for our stay."
Reuben Dimond House, Renovated Historic Farmhouse in the Capital, Concord, NH.
Pond Retreat: Beach, Kayak, Canoe, Deck, Firepit,
Exterior

Pond Retreat: Beach, Kayak, Canoe, Deck, Firepit,

9.0 out of 10, Wonderful, (11)
"We truly enjoyed our stay and hope to be back one day. The deck was a great place to chat and chill!"
Pond Retreat: Beach, Kayak, Canoe, Deck, Firepit,
Charming Lake Community Bungaloo. Comfortable living with 86 inch tv!
Property grounds

Charming Lake Community Bungaloo. Comfortable living with 86 inch tv!

10.0 out of 10, Exceptional, (4)
"Cute and comfortable home. Would stay again!!"
Charming Lake Community Bungaloo. Comfortable living with 86 inch tv!
Waterfront Lake Winnisquam House, Guest House & Barn Game Rm, Sleeps 16 w/ Beach
On the beach

Waterfront Lake Winnisquam House, Guest House & Barn Game Rm, Sleeps 16 w/ Beach

9.8 out of 10, Exceptional, (25)
"Perfect vacation spot just a short drive from Boston. The property is beautiful and had everything needed to make a great family vacation"
Waterfront Lake Winnisquam House, Guest House & Barn Game Rm, Sleeps 16 w/ Beach
Waterfront Home w/ Private Dock
Interior

Waterfront Home w/ Private Dock

10.0 out of 10, Exceptional, (15)
"Our family had a wonderful time at this lake house. It had everything we needed for cooking, playing in the lake and relaxing. Would definitely stay again! "
The price is AED 1,010
AED 1,574 total
includes taxes & fees
20 May - 21 May
Waterfront Home w/ Private Dock
Location, Location, Location
Fridge, microwave, oven, stovetop

Location, Location, Location

10.0 out of 10, Exceptional, (5)
"Nicely appointed, spacious, conveniently located."
Location, Location, Location
Perfect Modern Lake Front Retreat with Dock! Sleeps 4
Miscellaneous

Perfect Modern Lake Front Retreat with Dock! Sleeps 4

9.6 out of 10, Exceptional, (18)
"The place was quaint, modern and lovely. The views were fabulous! "
The price is AED 613
AED 1,092 total
includes taxes & fees
19 May - 20 May
Perfect Modern Lake Front Retreat with Dock! Sleeps 4
Renovated home with a water view, washer/dryer, AC, deck & wood stove
Terrace/patio

Renovated home with a water view, washer/dryer, AC, deck & wood stove

9.8 out of 10, Exceptional, (29)
"Comfortable home with great views."
Renovated home with a water view, washer/dryer, AC, deck & wood stove
Spacious New Hampshire mountain waterfront get away house. Boats & private docks
View from property

Spacious New Hampshire mountain waterfront get away house. Boats & private docks

9.8 out of 10, Exceptional, (38)
"Very nice place to stay Thank you"
Spacious New Hampshire mountain waterfront get away house. Boats & private docks
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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Other property types in Pittsfield

Postcard Cabins Blake Brook
Exterior

Postcard Cabins Blake Brook

2.0 star property
10.0 out of 10, Exceptional, (16)
"Quaint, Quiet, Peaceful Retreat"
The price is AED 459
AED 638 total
includes taxes & fees
22 May - 23 May
Postcard Cabins Blake Brook
Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock
Outdoor dining

Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock

9.6 out of 10, Exceptional, (20)
"Very peaceful spot, we had everything we needed."
Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
Indoor pool

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

10.0 out of 10, Exceptional, (168)
"House was great! Very short drive to gunstock mountain for skiing. The pool and hot tub was a big hit and a great way to spend some time post skiing.Highly recommended "
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
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.