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Compare 359 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
Private all Indoor Pool & Hot Tub, Sauna & steam room. Far end view of the pool

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

10.0 out of 10, Exceptional, (157)
"The location is exceptional. The pool area, steam room, sauna, and total recreation area were amazing. The pool temperature (air and water) was good for this time of year. The consistent 4 foot pool depth made it great for a community water volley ball game. (*We are all over 65) Having 5 "king bedrooms with three bathrooms in three different areas of the house allowed the entire adult group comfort and privacy. We also made use of the 2 bathrooms near the pool. The extra large living...
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
Deck For Entertaining: Belmont Group Getaway
Belmont Vacation Rental | 5BR | 4BA | 5,000 Sq Ft | Stairs Required

Deck For Entertaining: Belmont Group Getaway

9.0 out of 10, Wonderful, (65)
"This house was such a find. It sleeps so many adults comfortably. There is so much space and comfortable couches. The kitchen is well stocked with pans and platters, etc. Check in and check out were really easy. It was the best house we could have asked for."
Deck For Entertaining: Belmont Group Getaway
Reuben Dimond House, Renovated Historic Farmhouse in the Capital, Concord, NH.
Exterior

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

10.0 out of 10, Exceptional, (54)
"Wonderful stay in this beautiful historic property. Lynn greeted us at check in and gave us the full run down of the property and set the tone for a great long weekend away. Reliable wifi and a TV with all the apps if you're looking to stay connected and plenty of opportunities to disconnect with trails starting right out the front door, a fire pit, and books and games to take advantage of. Close to so many activities in the area but far enough away to enjoy total solitude as well."
Reuben Dimond House, Renovated Historic Farmhouse in the Capital, Concord, NH.
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

8.8 out of 10, Excellent, (15)
"We stay. In Alton Bay each year for a couple of concerts at Bank of NH Pavilion in Gilford. We extend it by staying for a couple of days at Lake Winnipesaukee The motel is perfectly located close to the venue and on the lake for swimming and boating while visiting BNH Pavilion. The motel is in a pine grove and is lake front. It's "!old school " feel reminds of my childhood. It's clean and quite, but no thrills. Don't expect first class accommodations but if you like the feel of a...
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
🏖 Lake Winnipesaukee Vacation at Akwa Marina 🏖 Beach, Pool, Hot Tub, Beach Bar
Steps away from the home, enjoy unlimited access to Beautiful Resort Marina

🏖 Lake Winnipesaukee Vacation at Akwa Marina 🏖 Beach, Pool, Hot Tub, Beach Bar

10.0 out of 10, Exceptional, (45)
"Such a wonderful stay for a girls’ weekend! The property was more than we expected. Beautiful views and a prime location to restaurants and shops. We had a such a great time. It was so homey and cozy. The porch looks out to Lake Winni and we watched the sunset and rise. The hosts were great and so easy to communicate with. Would 100% recommend!! Hoping to stay here again in the future :) "
🏖 Lake Winnipesaukee Vacation at Akwa Marina 🏖 Beach, Pool, Hot Tub, Beach Bar
Lakefront Home
View from living room

Lakefront Home

10.0 out of 10, Exceptional, (15)
"The house was absolutely perfect my family is planning to stay again "
Lakefront Home
Stargazer's retreat with hot tub & decks - near Ellacoya State Beach

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

8.6 out of 10, Excellent, (24)
"Nice home, close to bank of NH pavilion, and Weirs beach. "
Stargazer's retreat with hot tub & decks - near Ellacoya State Beach
Serene Retreat near Lake Winnipesaukee with Hot Tub & Modern Amenities
Hot tub with a privacy fence

Serene Retreat near Lake Winnipesaukee with Hot Tub & Modern Amenities

9.4 out of 10, Exceptional, (10)
"Big house, clean, full furnished, comfortable bed, hot tub is great! love this place, will come back again"
Serene Retreat near Lake Winnipesaukee with Hot Tub & Modern Amenities
Glass House Getaway- 3 Minutes to Gunstock & Pet Friendly!
The Glass House

Glass House Getaway- 3 Minutes to Gunstock & Pet Friendly!

10.0 out of 10, Exceptional, (53)
"The six of us spent the weekend playing board games and sleeping in comfortable beds. The space is roomy with plenty of furniture to fit a group or family. The yard is pleasant with a fire ring and chairs. I would definitely stay here again!"
Glass House Getaway- 3 Minutes to Gunstock & Pet Friendly!
Pet-Friendly Gilford Home by Gunstock Ski Mountain
Gilford Vacation Rental | 3BR | 2BA | 3,220 Sq Ft

Pet-Friendly Gilford Home by Gunstock Ski Mountain

9.4 out of 10, Exceptional, (13)
"The home was just as pictured. We had problems with the internet connection, but the management did their best to fix it. If they can fix the internet issue this home is perfect for a ski vacation! "
Pet-Friendly Gilford Home by Gunstock Ski Mountain
Enjoy some peace at Locke Lake Waterfront Retreat
Exterior

Enjoy some peace at Locke Lake Waterfront Retreat

10.0 out of 10, Exceptional, (36)
"First time seeing Fall colors in New England. This place did NOT disappoint !! Everything is well done! Truly enjoyed staying in Molly’s VRBO. "
Enjoy some peace at Locke Lake Waterfront Retreat
🌟 Newly Renovated Lakeside Haven – Your Premier Retreat! 🏡🌊🚤
Property grounds

🌟 Newly Renovated Lakeside Haven – Your Premier Retreat! 🏡🌊🚤

9.8 out of 10, Exceptional, (9)
"Great home and a beautiful lake made for a great stay for us and our teenagers. The beach club access was another big plus, with activities for all ages."
🌟 Newly Renovated Lakeside Haven – Your Premier Retreat! 🏡🌊🚤
Downtown Wolfeboro! Walk to the lake, restaurants and park
Kitchen Dining

Downtown Wolfeboro! Walk to the lake, restaurants and park

9.0 out of 10, Wonderful, (8)
"Myself, my parents and my 4 year old son stayed for 4 nights. The house appears to be remodeled recently and everything looked nicely designed. Comfortable beds made for restful night. Great location across a park for my son and walking distance to the tow. Only thing missing was that a hot tub was listed in the amenities which we did not see at the property. "
Downtown Wolfeboro! Walk to the lake, restaurants and park
Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock
Deck View of Lake

Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock

9.8 out of 10, Exceptional, (19)
"We had a very nice time just relaxing and doing nothing. With the holidays here we wanted to rest and enjoy the time."
Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock
3bd2ba hot tub - hiking, lake, fire pit, skiing
Hot Tub

3bd2ba hot tub - hiking, lake, fire pit, skiing

2.0 star property
3bd2ba hot tub - hiking, lake, fire pit, skiing
Waterfront home with wraparound deck, floating fireplace, deck, & firepit

Waterfront home with wraparound deck, floating fireplace, deck, & firepit

6.4 out of 10, (19)
"The house was nice but needs updates. The view was absolutely gorgeous and very easy to get too."
Waterfront home with wraparound deck, floating fireplace, deck, & firepit
Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room
Exterior

Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room

10.0 out of 10, Exceptional, (7)
"Great location, beautiful house , we were a bit upset that the outside hot tub was not available even though it was listed as part of the amenities."
Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room
Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock
Interior

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

10.0 out of 10, Exceptional, (86)
"Hanna was a wonderful host! When we had an issue with water pressure in the shower, she responded within minutes and had someone out to fix it within about an hour. The place is rustic but charming with a great fireplace!"
Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock
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, (43)
"The house had a generous layout with room to spread out and be comfortable. Sited right on the waterfront, it was a beautiful location. It’s all there - a hot tub, kayaks, pool table. We parked 4 cars too. Owner was responsive to anything that came up - our wayward Amazon package - even reaching out to mail carrier for help. Very accommodating! Would certainly return when we get a chance."
Charming and spacious lakefront home w/hot tub and pool table!
Lakefront, gameroom,Air Conditioner,firepit, kayaks, canoes, frog mat,pedal boat
Enjoy views of the lake from your 2nd floor deck with ceiling fan

Lakefront, gameroom,Air Conditioner,firepit, kayaks, canoes, frog mat,pedal boat

9.8 out of 10, Exceptional, (20)
"Well appointed, clearly newly updated. Bedrooms were on first and second floors which made it easier for couples, because the bathrooms were not in the bedrooms. It’s a beautiful property that I’m sure is wonderful year round. The only complaint was the garage was so cold we couldn’t utilize it."
Lakefront, gameroom,Air Conditioner,firepit, kayaks, canoes, frog mat,pedal boat
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

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
Private all Indoor Pool & Hot Tub, Sauna & steam room. Far end view of the pool

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

10.0 out of 10, Exceptional, (157)
"The location is exceptional. The pool area, steam room, sauna, and total recreation area were amazing. The pool temperature (air and water) was good for this time of year. The consistent 4 foot pool depth made it great for a community water volley ball game. (*We are all over 65) Having 5 "king bedrooms with three bathrooms in three different areas of the house allowed the entire adult group comfort and privacy. We also made use of the 2 bathrooms near the pool. The extra large living...
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
Deck For Entertaining: Belmont Group Getaway
Belmont Vacation Rental | 5BR | 4BA | 5,000 Sq Ft | Stairs Required

Deck For Entertaining: Belmont Group Getaway

9.0 out of 10, Wonderful, (65)
"This house was such a find. It sleeps so many adults comfortably. There is so much space and comfortable couches. The kitchen is well stocked with pans and platters, etc. Check in and check out were really easy. It was the best house we could have asked for."
Deck For Entertaining: Belmont Group Getaway
Reuben Dimond House, Renovated Historic Farmhouse in the Capital, Concord, NH.
Exterior

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

10.0 out of 10, Exceptional, (54)
"Wonderful stay in this beautiful historic property. Lynn greeted us at check in and gave us the full run down of the property and set the tone for a great long weekend away. Reliable wifi and a TV with all the apps if you're looking to stay connected and plenty of opportunities to disconnect with trails starting right out the front door, a fire pit, and books and games to take advantage of. Close to so many activities in the area but far enough away to enjoy total solitude as well."
Reuben Dimond House, Renovated Historic Farmhouse in the Capital, Concord, NH.
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.