Vacation rentals in Pittsfield

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Popular amenities for Pittsfield vacation rentals

Stay near Pittsfield's top sights

Main Street Bar And Grill8 locals recommend
White Buffalo Trading Post5 locals recommend
Appleview Orchard4 locals recommend
Chichester Country Store3 locals recommend
The Old Barnstead Country Store3 locals recommend
Moonlight Meadery Gift Shop & Outdoor Tasting Destination3 locals recommend

Other great vacation rentals in Pittsfield

Top guest favorite
Home in Thornton
4.98 out of 5 average rating, 66 reviews

Ridgeview - 70 acre White Mountain estate w/ views

KatRating, 5 stars1 week ago
We spent a bachelorette weekend here and absolutely loved the house (which is good cause we were inside a lot with bad weather). This place was even better than the photos - all the beds were comfy, the kitchen was well-outfitted with lots of cooking stuff, the amenities were great, and it had a secluded, cozy vibe. We loved the movie theater and the amazing living room, and all 9 of us could sit at the table and on the couch. I would definitely come back!
Guest favorite
Home in Hampton
4.9 out of 5 average rating, 79 reviews

Lux Getaway! Perfect for Groups 8+ppl

AhmedRating, 5 stars5 months ago
Josh and Tracy are very nice and friendly and their place is amazing! I highly recommend their place to anyone visiting the area!
Superhost
Home in Hampton Beach
4.81 out of 5 average rating, 26 reviews

Steps to Beach|Porch|Grill - The Sister Cottages

Donna SRating, 5 stars10 months ago
We had such a wonderful time . Both of our kids came with our 4 grandchildren, my Mom, sister and sister-in-law. The twelve of us had plenty of room to gather and to get the serenity we needed from time to time. The ocean is so soothing. We caught the most beautiful sunset ever over the marsh. Some of the locals told me it was the best they've ever seen in 30 years ! I'll be back! Thanks Chris. Ps. The pack-n-play was great too. 😆 🤣
Superhost
Home in Tamworth
4.82 out of 5 average rating, 96 reviews

Lakefront HotTub, Fireplace, Shop, Ski, Hike, Swim

ShaunaRating, 5 stars2 months ago
The place is clearly well taken care of with attention to detail. This would be a great place any time of year. Miriam and the home were very accommodating. I would return to this location with great peace of mind.
Top guest favorite
Home in Sandown
4.94 out of 5 average rating, 16 reviews

Sunrise Beach Escape

DebraRating, 5 stars1 day ago
This was the perfect location for our family to spend spring break together! The teenagers loved the games and hot tub, and the adults loved sitting on the patio and chit chatting. The beds were all comfortable, and the window air-conditioning units let each room pick their comfortable temperature. There is plenty of space in the kitchen, and the house had a ton of items available! They provided sufficient paper towels, toilet paper, and dishwasher soap (which so many do not) We all enjoyed the pinball enough that we definitely had to get an extra few rolls of quarters for our 5 night trip. We also all don't do well with the Melaluca brand products that the house uses, so we got our own soaps. There are so many great spaces on the property, and we would have spent even more time outdoors if the weather was warmer, but there was SO much to do inside! We all kept commenting how perfect it was for our group of 6 adults, 2 teens, and 2 tweens.
Guest favorite
Home in Freedom
4.9 out of 5 average rating, 94 reviews

Our Mountain Retreat – Lake Ossipee Access

FinRating, 5 stars1 month ago
Paula’s was the perfect spot for a weekend trip with a group of friends for my birthday! It had plenty of sleeping spots for us and was very comfortable, and we really loved the hot tub. They were such responsive and communicative hosts as well, and offered us a flexible late check-out. Thank you!
Guest favorite
Home in Holderness
4.9 out of 5 average rating, 10 reviews

Beautiful Home away from Home

StefanieRating, 5 stars1 month ago
My friends and I had a wonderful stay at this house hosted by Byron Property Management. They had snacks waiting for us when we arrived, Christina was kind and quick to respond when we had a question, and the house was exactly what was demonstrated in their advertisement. We are excited to come back next year and hopefully make this an annual trip at this property!
Top guest favorite
Home in Thornton
5 out of 5 average rating, 9 reviews

Spacious Private Home in White Mountains-Loon-Owl

KristenRating, 5 stars1 month ago
The house was perfect for a bigger group and had so much space! Great location and amenities-everything was labeled which was super helpful! The location was great for surrounding ski mountains (20 min to several), as well as other activities. Owners were very communicative and easy to reach if needed. Would love yo rent again!

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