
Holiday houses in Brattleboro
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Top-rated holiday rentals in Brattleboro
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Other great holiday rentals in Brattleboro
Guest favourite

Guesthouse in Brattleboro
4.93 out of 5 average rating, 70 reviewsCasita by the Green: Quiet, Country, close to town
GuangliangRating, 5 stars3 months ago
We had a fantastic stay at Cyndi’s place! She is an incredibly helpful and thoughtful host, going above and beyond to make sure we were comfortable. She even provided us with milk and cream, which was such a kind touch. The accommodation was clean, cozy, and well-equipped, making our stay even more enjoyable. Highly recommend staying here if you’re looking for a welcoming and hassle-free experience!
Top Guest favourite

Barn in Brattleboro
4.94 out of 5 average rating, 69 reviewsSunny barn apartment 4 minute walk from downtown
MadeleineRating, 5 stars1 week ago
Really enjoyed our three-day visit to Brattleboro with this home as our base. A beautiful 18th-century converted barn set in what's now a backyard garden behind a row of houses, a short walk from downtown, and with wooded trails right out back. Kathleen and Will live in the house up front and were pleasant and gave us plenty of space. The kids' bunk turned out to be a little too tight for our 8-year-old, but she slept comfortably on the couch. Really enjoyed the stash of books and games they keep on hand, and watching the wildlife visit the garden. Hope to come back and stay again next year.
Guest favourite

Farm stay in Brattleboro
4.91 out of 5 average rating, 93 reviewsModern Vermont Farm Stay
KaseyRating, 5 stars3 weeks ago
We wish we could have stayed longer! The apartment was so cozy, cute, and clean. It was a very quiet and peaceful but also convenient for getting to downtown Brattleboro. We visited the animals in the barn and met Chaya's friends who introduced us to each sheep and let us feed them snacks. Although we didn't meet Chaya in person, she was incredibly patient in helping me fix a booking error I made. We'd definitely come back.
Guest favourite

Home in Guilford
4.92 out of 5 average rating, 50 reviewsVermont Mirror House
GeorgeRating, 5 stars1 week ago
I was planning on my proposal and wanted somewhere special. The window house was exactly that. Private, peaceful, super clean, amazing views and wildlife. Taylor and Marla were EXTREMELY good at communicating and getting back in a timely manner. If you and your significant other are looking to get away, this is the place. It’s sublime.
Guest favourite

Cabin in West Brattleboro
4.94 out of 5 average rating, 18 reviewsEnchanted Woodland Cabin: Deck & Babbling Brook
RonnieRating, 5 stars5 days ago
Rented last minute for one night and everything went perfectly. Beautiful cottage in a beautiful location
Top Guest favourite

Apartment in Brattleboro
4.95 out of 5 average rating, 20 reviewsTranquil oasis with colorful touches
JoannaRating, 5 stars1 month ago
I just loved staying at Jen's sweet apartment. I was very busy doing work at another house during my stay and it was just so nice to come back to such a peaceful oasis to relax and recharge. The bed was extra comfy and I have honestly never slept in such a quiet bedroom before. Lots of sweet touches throughout, including teas, coffees, chocolates and some goodies in the fridge were so appreciated. It's obvious how much love and care were put into the space and it was such a treat to stay there! Thank you, Jen ❤️
Guest favourite

Home in West Brattleboro
4.97 out of 5 average rating, 30 reviewsBlack Dør Barn | Lux Brattleboro Nature Escape
PaigeRating, 5 stars5 days ago
We thoroughly enjoyed our stay at Coco’s place! Coco was a super host to be sure! She welcomed us with fresh local strawberries, flowers, and homemade sparkling water…possibly the best strawberries and sparkling water we’ve ever had! Coco communicated quickly and was very kind and generous. The house was absolute perfection inside and out. Very spacious with privacy for each traveler…it has a cozy, minimalist feel with a European flair. Coco has paid attention to even the smallest detail in the design & decor and truly cares about the comfort of her guests. The property is beautiful and serene and very well-kept. There’s lots of outdoor space with comfortable seating and lounging. We had a short scenic drive (10 minutes) to town for food and attractions. We would definitely stay at Coco’s place again and highly recommend it to other guests!
Guest favourite

Home in West Brattleboro
4.92 out of 5 average rating, 50 reviewsBeautiful nature retreat minutes to downtown
AlexRating, 5 stars7 months ago
This little apartment is perfect if you are looking for a quiet and relaxing getaway. There is no TV, and it is in the middle of the woods, which is exactly the vibe we wanted. You could go outside and hear a pin drop. Sarah was super helpful and responsive and gave us all kinds of local recommendations and some based off where we were going for the weekend. She also left a bottle of wine which was very nice and was enjoyed! The entrance is private - you actually can't see it from the main house since the door is on the back of the building. One note about the bed if you are someone who needs a squishier mattress - the one here is pretty firm, but it felt like maybe it was a type of memory foam? Much firmer than the mattress we have at home, but we still slept pretty well. Just a note for those of you who absolutely can't deal with a firmer bed. The best part is that even though you're in the middle of the woods, you're still only 8 minutes from downtown, so right near everything!
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