Search Vacation Homes in Pittsfield

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

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

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

Serene getaway with private sauna, firepit, deck, grill, balcony, & washer/dryer

8.8 out of 10, Excellent, (19)
"The moment you walk in you feel like you are home. The view was perfect in living area and up stairs bedroom. Even in the kitchen you felt like you could be apart of the conversation happening in the living area. It is a house my friends and I decide that it would be a house we would love to come back to in the future."
Serene getaway with private sauna, firepit, deck, grill, balcony, & washer/dryer

🌟 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! 🏡🌊⛰️

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

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, (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.

Lakefront Home

10.0 out of 10, Exceptional, (15)
"The house was absolutely perfect my family is planning to stay again "
Lakefront Home

New Hampshire Winter Retreat near Gunstock mountain for 10

10.0 out of 10, Exceptional, (4)
"The place was spacious and clean. Communication was prompt. Location was convenient for lake/beach/town. Had a wonderful time and would definitely stay again! "
The price is HK$3,892
HK$4,822 total
includes taxes & fees
26 Nov - 27 Nov
New Hampshire Winter Retreat near Gunstock mountain for 10

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, (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

Spacious Belmont Home w/ Seasonal Pool & Grill!

9.0 out of 10, Wonderful, (65)
"We had an amazing experience here! From booking to check-in to the weekend stay, everything was smooth and easy. Robert was excellent with answering questions, allowing an early check-in and an extended checkout, and was very responsive with communication. I met property managers Brandon, Jared, and Craig when I arrived and they were super helpful (and gave a great pizza delivery recommendation)! The house was exactly as advertised. Plenty of space for our group, clean and organized, and...
Spacious Belmont Home w/ Seasonal Pool & Grill!

NEW Lakeside Haven: Sleeps12| HotTub |Private Dock

9.0 out of 10, Wonderful, (26)
"Very enjoyable home! Perfect spot right on the water. "
The price is HK$2,483
HK$4,979 total
includes taxes & fees
25 Nov - 26 Nov
NEW Lakeside Haven: Sleeps12| HotTub |Private Dock

Webster Lake Retreat for Nature and Water Lovers

9.6 out of 10, Exceptional, (17)
"This house is perfect for a family trip. It is in a perfect location and has stunning views"
Webster Lake Retreat for Nature and Water Lovers

Dog-friendly retreat nestled near the tranquil pond shore with spacious deck

9.6 out of 10, Exceptional, (4)
"In town for my brother in laws wedding. Clean, great location. Everything you need."
Dog-friendly retreat nestled near the tranquil pond shore with spacious deck

Lakefront Retreat w/ Kayaks, Grill, Fire Pit!

9.6 out of 10, Exceptional, (10)
"We went in November for a small family retreat and did expect to nor did we swim or kayak. But being on the lake, sitting on the dock and small beach was a magical way to see so many many stars in the sky. It was steps to walk into Pawtuckaway park and go in a hike. We made it to the fire tower!"
Lakefront Retreat w/ Kayaks, Grill, Fire Pit!

Winnisquam Lake House

10.0 out of 10, Exceptional, (26)
"We stayed at this property the weekend of our son's wedding. It was perfect size for my wife and I along with the rest of our family (12 in all ranging from 8 yrs old). Very neat with all the accommodations needed for any length of stay. Marcela who is the property owner could not have been more pleasent and helpful. Check in was a breeze and she was a great communicator. "
Winnisquam Lake House

Smith's Point Retreat on Lake Winnipesaukee with indoor pool!

8.4 out of 10, Very good, (5)
"We stayed between Christmas and New Years to go skiing at Gunstock - it rained 2 out of the 3 days but the house was so great with the indoor pool we didn't mind being stuck inside. We had an issue with the TV in the pool area and someone came out to look at it for us which was appreciated. Only thing I would recommend is adding a hot tub! Great place and thinking of renting again in the summer to enjoy the lake!"
Smith's Point Retreat on Lake Winnipesaukee with indoor pool!

Idyllic Mountain and Lake Getaway

10.0 out of 10, Exceptional, (51)
"We had an absolutely amazing weekend at this peaceful mountain escape! Our friends all enjoyed the amenities, the lovely toiletries the host left, and the fire pit on the deck was the perfect spot for nighttime conversations. Will definitely be back."
The price is HK$2,335
HK$5,312 total
includes taxes & fees
25 Nov - 26 Nov
Idyllic Mountain and Lake Getaway

Gorgeous Waterfront with Dock & Mountain Views on Winnisquam - Sleeps 12

10.0 out of 10, Exceptional, (30)
"This was our second year celebrating the summer as a company at this location. Beautiful home and lake!"
Gorgeous Waterfront with Dock & Mountain Views on Winnisquam - Sleeps 12
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

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

Spacious Belmont Home w/ Seasonal Pool & Grill!

9.0 out of 10, Wonderful, (65)
"We had an amazing experience here! From booking to check-in to the weekend stay, everything was smooth and easy. Robert was excellent with answering questions, allowing an early check-in and an extended checkout, and was very responsive with communication. I met property managers Brandon, Jared, and Craig when I arrived and they were super helpful (and gave a great pizza delivery recommendation)! The house was exactly as advertised. Plenty of space for our group, clean and organized, and...
Spacious Belmont Home w/ Seasonal Pool & Grill!

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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.