Holiday Rentals in Pittsfield

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Holiday Rentals 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.

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

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

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, 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

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

New Hampshire Getaway w/ Game Room & Lake Access

9.6 out of 10, Exceptional, (4)
"Great layout- loved the porch/deck at night Game room is an amazing addition Everyone loved it!"
New Hampshire Getaway w/ Game Room & Lake Access

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

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

All-Season Cozy Lakeside Cabin in Northwood, NH- 2 Bdr, great views

10.0 out of 10, Exceptional, (25)
"Great location. There are neighbors, but you feel like you are all alone. Perfect for relaxation by the fire. Would definitely go back."
All-Season Cozy Lakeside Cabin in Northwood, NH- 2 Bdr, great views

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!

Winnipesaukee Lakefront Home with Dock & Views!

9.4 out of 10, Exceptional, (61)
"Interior of the home was very nice. Access to water was difficult and made worse by the lack of pruning of the bushes that had grown into the already narrow stairway leading to the dock. Parking was difficult, additional information regarding possible places to park another vehicle or trailer would be helpful. A broom and functioning vaccum would also have been helpful. Dock boards, posts, and cletes, were loose in multiple locations with exposed nails facing upwards. Multiple dirty dishes in...
Winnipesaukee Lakefront Home with Dock & Views!

Delightful cabin lake views & access now featuring AC Wi-FI and TV sleeps 3

9.0 out of 10, Wonderful, (8)
"Great little place, only bad was TV did not work properly and kept turning itself on for no reason. It was late season and not much soap in shower (not a big deal) other than that, super clean, nice fire pits and PLENTY of chairs. Cabin itself was VERY clean, It was a great after concert sleep. "
Delightful cabin lake views & access now featuring AC Wi-FI and TV sleeps 3

Stay at Gilford Resort/Ski Gunstock/ 10 min. Drive to Gunstock

9.6 out of 10, Exceptional, (131)
"We really enjoyed our stay. The condo was comfortable, clean, had everything you needed and was in a great location. We enjoyed walking across the street to the lake and up the hill to go the concert next door. We were also a short drive from Weirs Beach. We had great communication and hope to stay there again."
Stay at Gilford Resort/Ski Gunstock/ 10 min. Drive to Gunstock

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.

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

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

The Hideaway, lake views & access sleeps 8 Now featuring AC Wi-FI and TV

9.8 out of 10, Exceptional, (7)
"Nice location close to Alton Bay. The Hideaway #10 was comfortable and well appointed. A bit more attention to the bedroom, kitchen and grill cleanliness would make it perfect."
The Hideaway, lake views & access sleeps 8 Now featuring AC Wi-FI and TV
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 types of properties in Pittsfield you may be interested in

Comfort Inn Concord

2.5 star property
8.4 out of 10, Very good, (1003)
"My stay was nice. Friendly staff. Nice complimentary breakfast. Hot tub was being serviced, unfortunately. Saltwater pool was lovely."
The price is €101
includes taxes & fees
22 Dec - 23 Dec
Comfort Inn Concord

The Centennial

4.0 star property
8.8 out of 10, Excellent, (858)
"Charming"
The price is €167
includes taxes & fees
4 Dec - 5 Dec
The Centennial

Steele Hill Resorts

3.0 star property
8.4 out of 10, Very good, (573)
"Beautiful place"
The price is €165
includes taxes & fees
24 Nov - 25 Nov
Steele Hill Resorts
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.

Frequently asked questions

Can I find holiday rentals in Pittsfield?

Yes, there are holiday rentals close to the most popular sights in Pittsfield, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Pittsfield has to offer?

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski: This holiday home rental outside of Pittsfield is located on a lake, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

What’s there to see and do in Pittsfield?

While exploring the area, visit family-friendly sights like Christa McAuliffe Planetarium, or get outside and enjoy nature at Suncook River. In the wider area, you’ll find New Hampshire International Speedway and Bow Lake.

What’s a holiday rental in Pittsfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pittsfield. Holiday rentals provide amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for a small group gathering.