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Check prices for these dates

Compare 439 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

Safe Peaceful Quite Bright Gorgeous Accessibility

The price is SAR 844
SAR 1,514 total
includes taxes & fees
30 Apr - 1 May
Safe Peaceful Quite Bright Gorgeous Accessibility

Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock

9.6 out of 10, Exceptional, (20)
"As a family of 6, our options are limited to 2 hotel rooms or a vacation property. This property exceeded all expectations. Perfect balance between feeling like a family vacation home and an elevated rental property without being full luxury with the typical higher price tag. Will definitely return. "
The price is SAR 375
SAR 1,575 total
includes taxes & fees
27 Apr - 28 Apr
Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock

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

9.8 out of 10, Exceptional, (31)
"Roomy, sunny cape only 8 minutes to the slopes. The place was clean, bright, and had everything we needed. 10 minutes to Walmart or Hannaford for what we forgot to bring. Loved the claw foot tub with bubble bath and a view of snow covered pines. Thank you for sharing your home"
Updated Cape home with WiFi, W/D, full kitchen & clawfoot tub

Six-Bedroom Family Retreat Near Portsmouth

Six-Bedroom Family Retreat Near Portsmouth

Barn Off the beaten path yet close to everything.

10.0 out of 10, Exceptional, (16)
"Excellent place to stay. Girlfriend and I wanted a place to get away from the city for a weekend and this was it. It has everything you need plus the quiet you came for. Would recommend to anyone thinking about booking a stay. "
Barn Off the beaten path yet close to everything.

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

10.0 out of 10, Exceptional, (167)
"Fantastic stay! The house was spotless, beautifully decorated, and had all the amenities we needed for a comfortable stay. The location was perfect—close to everything yet peaceful and relaxing. The host was responsive and made the check-in process seamless. Highly recommend and would definitely stay again!"
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

9.8 out of 10, Exceptional, (97)
"The hosts are super attentive, communicative and the check in could not have been easier. The place was super clean with all utensils, plates and kitchen supplies. There is an extended dog leash in the backyard so your pup can explore safely. Overall would recommend, the fireplace in particular was amazing to use."
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

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!

10.0 out of 10, Exceptional, (48)
"We very much enjoyed staying at this cottage. It reminded us of a location our family had on Hills Pond."
Charming and spacious lakefront home w/hot tub and pool table!

Waterfront with Fire Pit, Pergola, close to gunstock and Downtown

9.8 out of 10, Exceptional, (28)
"My girlfriend and I had a weekend of peace and quiet by the river sitting next to the fire. Played some pool and air hockey. Very nice place to stay and enjoy all the comforts of home."
The price is SAR 596
SAR 1,188 total
includes taxes & fees
28 Apr - 29 Apr
Waterfront with Fire Pit, Pergola, close to gunstock and Downtown

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

10.0 out of 10, Exceptional, (63)
"We stayed at the Reuben Dimond House for 4 nights and had a wonderful time. The location was peaceful, quiet and secluded. The 1700’s home was authentic with modern amenities and convenience. We would definitely stay at the property again."
Reuben Dimond House, Renovated Historic Farmhouse in the Capital, Concord, NH.

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

9.0 out of 10, Wonderful, (11)
"We had a wonderful time at this house on the lake. We had coffee and cocktails on the dock and watch the beautiful sunsets and sunrise.Did some fishing ! Owners have a house next door and they are very nice . Ate dinner on the back patio. House was clean and well supplied. Could have used another AC unit on first floor ....and a TV on the first floor ...and cleaning supplies. Other than that ....very nice ! "
Pond Retreat: Beach, Kayak, Canoe, Deck, Firepit,

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

10.0 out of 10, Exceptional, (3)
"Great property, loaded with amenities. Super Clean. Exactly as described. Great stay!"
The price is SAR 739
SAR 1,697 total
includes taxes & fees
28 Apr - 29 Apr
Charming Lake Community Bungaloo. Comfortable living with 86 inch tv!

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

9.8 out of 10, Exceptional, (25)
"The lake house was the perfect fall escape for us! Extremely comfortable inside and out, with a well equipped kitchen. The bunkhouse and barn were so well done and gave us plenty of options for activities. And the views of the lake from early morning to late at night were breathtaking! I wouldn't hesitate renting the property again."
Waterfront Lake Winnisquam House, Guest House & Barn Game Rm, Sleeps 16 w/ Beach

Waterfront Home w/ Private Dock

10.0 out of 10, Exceptional, (14)
"This is a great little get away location. The pond neighborhood is quiet and everything is well maintained. Squirrel friends to watch gather nuts and ducks to calm the soul. "
The price is SAR 1,032
SAR 1,608 total
includes taxes & fees
29 Apr - 30 Apr
Waterfront Home w/ Private Dock

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

9.6 out of 10, Exceptional, (17)
"The place was quaint, modern and lovely. The views were fabulous! "
The price is SAR 863
SAR 1,422 total
includes taxes & fees
27 Apr - 28 Apr
Perfect Modern Lake Front Retreat with Dock! Sleeps 4

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

9.8 out of 10, Exceptional, (29)
"Great property and perfect for family stay. We used it as a base for ski races at Gunstock, only 10 minutes away. Fantastic waterfront property and views are outstanding. We would definitely come back. "
Renovated home with a water view, washer/dryer, AC, deck & wood stove

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

9.8 out of 10, Exceptional, (38)
"We had a great week with our kids and grandkids! Plenty of sleeping areas, and large living space for all 12 of us. We would have liked to have a bigger (flatter) lawn area for outdoor games, but the lake certainly made up for it. Host was attentive and responsive. We would stay here again. "
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

2.0 star property
10.0 out of 10, Exceptional, (13)
"This place is amazing. It was so quiet that I found myself whispering. Our dog loved it and she’s usually stressed out on trips. My only regret is only booking one night. "
The price is SAR 422
SAR 600 total
includes taxes & fees
20 May - 21 May
Postcard Cabins Blake Brook

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

10.0 out of 10, Exceptional, (167)
"Fantastic stay! The house was spotless, beautifully decorated, and had all the amenities we needed for a comfortable stay. The location was perfect—close to everything yet peaceful and relaxing. The host was responsive and made the check-in process seamless. Highly recommend and would definitely stay again!"
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

Cedar Lodge condo with mountain & lake Winnipesauke views!

9.6 out of 10, Exceptional, (40)
"I stayed at Cedar Lodge while at ski races at Gunstock. I was by myself and the condo was perfect for me. The snacks and bottled water were a nice touch. It was a great visit.Thank You,Bruce"
The price is SAR 177
SAR 556 total
includes taxes & fees
30 Apr - 1 May
Cedar Lodge condo with mountain & lake Winnipesauke views!
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.