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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
14 Apr - 15 Apr
Safe Peaceful Quite Bright Gorgeous Accessibility

Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock

9.8 out of 10, Exceptional, (21)
"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 581
SAR 1,836 total
includes taxes & fees
28 Apr - 29 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 w/ Hot tub, Theater

Six-Bedroom Family Retreat Near Portsmouth w/ Hot tub, Theater

Barn Off the beaten path yet close to everything.

10.0 out of 10, Exceptional, (14)
"Everything was great about this stay. Very clean place set off the road a little but only a few minutes from all the shops. Stairs and everything were shoveled and salted when we got there and there was more close by if we needed it. Left during a snow storm and the host was very nice and plowing the road which helped a lot. Definitely going to be staying here again!"
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)
"Massive 7,000 sq ft. super cool house close to Gunstock that felt like we rented an entire commercial lodge. Bedrooms and baths for everyone, large indoor pool, hot tub, steam and sauna, bar area, game room, and huge fireplaced dining room with seating for 20! Kids were ecstatic and we had the best time. Clean, responsive and pleasant owner as well. If you have a large family, this is the place...you won't be disappointed!PatrickMarshfield, MA"
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, (96)
"I met up with a friend who lives 3 states away now...So we decided to have a weekend get-together - this was the perfect place! Clean and comfortable. The couch and chairs were very comfortable, beds were very comfortable, the kitchen was well-supplied. We had a great time, and the hosts were very accessible. There had been a strong wind storm that had affected the utilities, but the hosts stayed informed and in touch with us, and everything was taken care of in a timely manner. I would...
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

8.4 out of 10, Very Good, (28)
"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, (47)
"The place was really warm, bright, clean and fun. The hot tube was great, the back deck area / waters edge was easy to access without 500 steps, Kareoke machine was going the whole time. Kitchen was great, we cooked every meal for the 3 days. Gas pressure is a little low on the cooktop but it all worked just fine. The 2 story sun room is really nice to read in. Beds were comfy and bathrooms were clean. The tub/shower valve is a little counter intuitive but we figured it out. Having a...
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, (27)
"The property was very clean. It had all we needed "
The price is SAR 784
SAR 1,433 total
includes taxes & fees
31 Mar - 1 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, (62)
"Beautiful house and location. Our only complaints would be that the house itself was fairly loud (creaky floors and no insulation between rooms so can hear when someone is up early or late) and sheer white curtains (making everyone have to get up with the sun), BUT all that said, wonderful old house. Very clean, well maintained, and stocked with everything you'd need. Would definitely recommend!"
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 529
SAR 1,441 total
includes taxes & fees
31 Mar - 1 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
31 Mar - 1 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
13 Apr - 14 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, (27)
"We stayed for six nights and had a very enjoyable stay. The views of the lake from the kitchen and common areas are unbeatable. Beds and bedrooms were comfortable. We didn’t mind the steps from the parking area, but as noted, they wouldn’t be good for people with mobility problems. We would have appreciated a binder with all the necessary information on the home, area restaurants, etc, including instructions on using the wood burning stove (we tried using it but had to stop due to smoke). ...
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, (11)
"Wondering. Had a great time"
The price is SAR 506
SAR 549 total
includes taxes & fees
14 Apr - 15 Apr
Postcard Cabins Blake Brook

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

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

Cedar Lodge condo with mountain & lake Winnipesauke views!

9.6 out of 10, Exceptional, (39)
"Great location and beautiful sunrise/sunset. The condo looks spot on to the listing. We appreciated the extra toiletries and snacks. Unfortunately we noticed crumbs/food all over the couch when we arrived. Overall, we we had a good experience."
The price is SAR 197
SAR 521 total
includes taxes & fees
3 Apr - 4 Apr
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.