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Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Pittsfield Vacation Homes

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

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

9.8 out of 10, Exceptional, (175)
"Fantastic stay! The house was spotless, beautifully decorated, and had all the amenities we needed for a comfortable stay. The location was perfect—close to everything yet peaceful and relaxing. The host was responsive and made the check-in process seamless. Highly recommend and would definitely stay again!"
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
great location weirs beach area rental
Outdoor dining

great location weirs beach area rental

9.4 out of 10, Exceptional, (21)
"The property was exactly as it was listed, The host was great"
The price is CA $496
CA $615 total
includes taxes & fees
Aug 25 - Aug 26
great location weirs beach area rental
Waterfront home with wraparound deck, floating fireplace, deck, & firepit
TV, DVD player

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

6.8 out of 10, (29)
"Just did a little getaway with some friends place was super cute and clean cute little area. Will definitely be booking for the summer."
Waterfront home with wraparound deck, floating fireplace, deck, & firepit
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette
Outdoor dining

Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette

9.0 out of 10, Wonderful, (21)
"Excellent"
The price is CA $178
CA $391 total
includes taxes & fees
Aug 25 - Aug 26
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette
Charming 2-bedroom house with WiFi and W/D in Alton Bay-10 min to Gunstock
Terrace/patio

Charming 2-bedroom house with WiFi and W/D in Alton Bay-10 min to Gunstock

10.0 out of 10, Exceptional, (1)
"The house is fine, clean, and well-maintained. I think the price is a bit too high for a two-bedroom apartment of this standard. The owner is very friendly and caring.Thank you"
Charming 2-bedroom house with WiFi and W/D in Alton Bay-10 min to Gunstock
Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock
Terrace/patio

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

9.8 out of 10, Exceptional, (102)
"Such a cozy cabin. Loved our stay."
Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock
The Cottages at Harvey Lake
Exterior

The Cottages at Harvey Lake

3.0 star property
8.8 out of 10, Excellent, (45)
"The view of the lake from the cabin was excellent. "
The price is CA $188
CA $204 total
includes taxes & fees
Sep 2 - Sep 3
The Cottages at Harvey Lake
Safe Peaceful Quite Bright Gorgeous Accessibility
Exterior

Safe Peaceful Quite Bright Gorgeous Accessibility

7.8 out of 10, Good, (14)
"In town for a few days hunting with friends. Place was nice and owner was nice. Had trouble with the door lock code a few times. Almost had reservation cancelled because the owner could “hear animals” which was actually us getting our turkey calls out for the following day. Very clean house and quiet neighborhood. Felt weird that the owner was in some sort of a hidden apt. though. "
Safe Peaceful Quite Bright Gorgeous Accessibility
🌟 Newly Renovated Lakeside Haven – Your Premier Retreat! 🏡🌊🚤
Outdoor pool

🌟 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! 🏡🌊🚤
Quaint Cottage in Private Wooded Setting | Close to Lakes | Dogs Welcome
Terrace/patio

Quaint Cottage in Private Wooded Setting | Close to Lakes | Dogs Welcome

9.8 out of 10, Exceptional, (43)
"This is our third stay at this sweet lake cottage—it has become like a little slice of home away from home! Love the bright cheery decor and perfect location. Julie is a wonderful and gracious host and always very responsive and considerate.We highly recommend!!"
Quaint Cottage in Private Wooded Setting | Close to Lakes | Dogs Welcome
Lakehouse 300 ‘ shore with 40' Dock, 10 Kayaks & kayak launch, boats & Fire pit
Terrace/patio

Lakehouse 300 ‘ shore with 40' Dock, 10 Kayaks & kayak launch, boats & Fire pit

9.8 out of 10, Exceptional, (69)
"It was great"
Lakehouse 300 ‘ shore with 40' Dock, 10 Kayaks & kayak launch, boats & Fire pit
Stargazer's retreat with hot tub & decks - near Ellacoya State Beach
Outdoor spa tub

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

8.0 out of 10, Very good, (35)
"Everything was clean, organize and had plenty of everything we needed in kitchen, bathroom, etc. The hot tub was a plus also!! Thank you for making our stay for our sons wedding an enjoyable one."
Stargazer's retreat with hot tub & decks - near Ellacoya State Beach
Waterfront with Kayaks, Pool Table, Fire Pit, and Pergola. Downtown area
Terrace/patio

Waterfront with Kayaks, Pool Table, Fire Pit, and Pergola. Downtown area

9.8 out of 10, Exceptional, (31)
"My girlfriend and I had a weekend of peace and quiet by the river sitting next to the fire. Played some pool and air hockey. Very nice place to stay and enjoy all the comforts of home."
The price is CA $413
CA $681 total
includes taxes & fees
Sep 8 - Sep 9
Waterfront with Kayaks, Pool Table, Fire Pit, and Pergola. Downtown area
Lakefront home with hot tub, beach, skiing nearby in tranquil Barnstead
Property grounds

Lakefront home with hot tub, beach, skiing nearby in tranquil Barnstead

10.0 out of 10, Exceptional, (6)
"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 hot tub, beach, skiing nearby in tranquil Barnstead
Lake, grill, s'mores, hike, golf! 4Bd 2.5Bath, sleeps10
Fridge, microwave, oven, stovetop

Lake, grill, s'mores, hike, golf! 4Bd 2.5Bath, sleeps10

10.0 out of 10, Exceptional, (12)
"Overall our stay was good and owner is super responsive. "
The price is CA $422
CA $951 total
includes taxes & fees
Sep 16 - Sep 17
Lake, grill, s'mores, hike, golf! 4Bd 2.5Bath, sleeps10
Rustic Lake front cottage nestled in the pines with a Golf Putting Green.
Smart TV, fireplace

Rustic Lake front cottage nestled in the pines with a Golf Putting Green.

3.0 star property
8.4 out of 10, Very good, (7)
"My family stayed in this beautiful home for 6 nights and we couldn’t have loved it more. The description matched the place perfectly. There was plenty of sleeping space for 6 adults and the view from the back porch was unreal. There was plenty of water supplies which gave everyone an equal opportunity to be out in the water. Would definitely stay here again!"
Rustic Lake front cottage nestled in the pines with a Golf Putting Green.
Spacious 4-bedroom house with, Private Beach, WiFi, AC in peaceful Alton
TV, fireplace

Spacious 4-bedroom house with, Private Beach, WiFi, AC in peaceful Alton

10.0 out of 10, Exceptional, (1)
"Great location, nice house, easy check in. Overall a very good experience for us."
Spacious 4-bedroom house with, Private Beach, WiFi, AC in peaceful Alton
Six-Bedroom Family Retreat Near Portsmouth
Property grounds

Six-Bedroom Family Retreat Near Portsmouth

7.6 out of 10, Good, (4)
"We booked this home for family visiting for a wedding. The group appreciated the comfortable rooms with nice private rooms, a bunk room, and a lovely large room with a beautiful window overlooking the wooded back yard. The group especially loved using the hot tub and the theater room!! It made their visit feel special and we appreciated the close proximity to our event. "
Six-Bedroom Family Retreat Near Portsmouth
NEW! Juniper Retreat POOL+HOT TUB
Fridge, microwave, oven, stovetop

NEW! Juniper Retreat POOL+HOT TUB

9.0 out of 10, Wonderful, (2)
"We stayed 2 nights at this lovely little house. The kitchen had everything we needed to cook our meals. Plenty of room for us to spread out and relax. Very close to fun stuff Laconia. The hot tub room was perfect since we had some rain, we were still able to enjoy the hot tub."
NEW! Juniper Retreat POOL+HOT TUB
7 Mi to Hiking: Waterfront Long Pond Gem!
TV, fireplace, video games, foosball

7 Mi to Hiking: Waterfront Long Pond Gem!

2.0 star property
9.0 out of 10, Wonderful, (4)
"Once you put your feet up by the fire and gaze out on to the pond, watch all the stress evaporate from your body. Our stay was awesome. We recommend staying here and plan on making it an annual trip. We want to thank our hosts for having everything we needed for an enjoyable and comfortable stay. Cheers, Mark "
7 Mi to Hiking: Waterfront Long Pond Gem!
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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Top Pittsfield Hotel Reviews

Tilton Lodge Inn and Suites

Tilton Lodge Inn and Suites

10/10 Excellent
"Very reasonable price for summer. Dated but clean. "
Craig 1-night trip
Posted 10 hours ago
Tilton Lodge Inn and Suites