Pittsfield Vacation Rentals

Browse Select Pittsfield Vacation Homes

Deck For Entertaining: Belmont Group Getaway

9.0 out of 10, Wonderful, (66)
"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

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

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

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

10.0 out of 10, Exceptional, (57)
"We thoroughly enjoyed our recent stay at this beautifully restored 257 year old farmhouse. The location was peaceful and private — truly an unexpected gem within minutes of the center of New Hampshire’s capital city. During our stay we experienced two snowstorms and we were grateful for our host’s balance of respecting our privacy while also ensuring us safe access in and out of the snowy property. We can’t wait to return in June and again in September! "
Reuben Dimond House, Renovated Historic Farmhouse in the Capital, Concord, NH.

SPECTACULAR LAKEFRONT VIEW WITH MOVIE THEATRE AND BOAT DOCK ALTON BAY NH

9.2 out of 10, Wonderful, (10)
"Great place. Plenty of room for 16 of us. Great ourdoor areas. Kids loved the movie room and the hot tub. Lake used every day. "
SPECTACULAR LAKEFRONT VIEW WITH MOVIE THEATRE AND BOAT DOCK ALTON BAY NH

🌟 Lakefront Bliss Awaits – Your Ultimate Getaway! 🏡🌊⛰️

9.2 out of 10, Wonderful, (25)
"Our group of 8 enjoyed the spacious house and proximity to the lake. The no contact check in was great. "
🌟 Lakefront Bliss Awaits – Your Ultimate Getaway! 🏡🌊⛰️

🏖 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

Waterfront private quiet family home, 15 min from Lake Winnipesaukee

10.0 out of 10, Exceptional, (18)
"From start to finish we had such an amazing stay. The property was even better than advertised, the pictures although gorgeous cannot capture what the property is. We will be renting again as everyone had such a great time. We were close enough to see what we wanted to see but honestly we could have stayed at the property the entire time there was plenty to do and see. Looking forward to returning!!"
Waterfront private quiet family home, 15 min from Lake Winnipesaukee

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

On Lake Winnipesaukee!,Year round house, private beach and great yard

8.6 out of 10, Excellent, (30)
"The location was perfect. Lake Winnipesauke is a massive lake. Having the home in a cove made the water calmer and easier to use boats and water ski. The property has a big sandy beach and a large pier. We were able to dock our boat and jet ski on the pier. They provided three kayaks and a paddleboard to use that were wonderful. The home was older but functional. The kitchen was stocked with everything you need to cook (minus crock pot). Plenty of dishes, utensils, serving plates,...
On Lake Winnipesaukee!,Year round house, private beach and great yard

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

10.0 out of 10, Exceptional, (37)
"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! 🏡🌊🚤

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

9.2 out of 10, Wonderful, (9)
"We came to Wolfeboro to celebrate Thanksgiving with family in town. The location was ideal with easy access to town. The house was immaculate and comfortable. We will rent again. "
Downtown Wolfeboro! Walk to the lake, restaurants and park

Lakefront home with beach, skiing nearby, AC and WiFi in tranquil Barnstead

10.0 out of 10, Exceptional, (1)
"The host Lauren was incredibly responsive, friendly, and accommodating. The check-in process was smooth and hassle-free. The house was, cleanliness, exceeded my expectations, along with the cozy decor, breathtaking view made it feel like a home away from home. I would absolutely recommend this property to anyone visiting that area and would love to return in the future! "
Lakefront home with beach, skiing nearby, AC and WiFi in tranquil Barnstead

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

2.0 star property
10.0 out of 10, Exceptional, (1)
3bd2ba hot tub - hiking, lake, fire pit, skiing

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

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

10.0 out of 10, Exceptional, (88)
"This little cabin provided a great place for me and my son to heal after the death of his mom, my wife.thank you Hanna"
Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock

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

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

10.0 out of 10, Exceptional, (54)
"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!
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.
Don't see what you're looking for?
See all available properties in Pittsfield
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Pittsfield

Cozy, Pet-Friendly Escape Near Lake & Mountains

10.0 out of 10, Exceptional, (23)
"Beautiful home. Great weekend away!! "
Cozy, Pet-Friendly Escape Near Lake & Mountains

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

Beach View at Chestnut Cove, Lake Winnipesaukee.

8.8 out of 10, Excellent, (12)
"Good place to stay would rent again."
Beach View at Chestnut Cove, Lake Winnipesaukee.
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.