
Vacation rentals in Pittsfield
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Top-rated vacation rentals in Pittsfield
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Top guest favorite

Home in Thornton
4.98 out of 5 average rating, 66 reviewsRidgeview - 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 reviewsLux 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 reviewsSteps 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 reviewsLakefront 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 reviewsSunrise 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 reviewsOur 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 reviewsBeautiful 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 reviewsSpacious 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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- Hampton Beach
- Wells Beach
- North Hampton Beach
- Ogunquit Playhouse
- Long Beach
- Pats Peak Ski Area
- Owl's Nest Resort
- Ragged Mountain Resort
- Monadnock State Park
- Long Sands Beach
- Purity Spring Resort
- Rye North Beach
- King Pine Ski Area
- Tenney Mountain Resort
- Wentworth by the Sea Country Club
- Manchester Country Club - NH
- Canobie Lake Park
- Bald Peak Colony Club
- Parsons Beach
- Mothers Beach
- Crescent Beach
- Ferry Beach
- Baker Hill Golf Club
- Bear Brook State Park
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