Vermont Vacation Homes Near Woodstock Private. Peaceful. Dog-Friendly

Tucked away on 18 private acres in Hartland, Vermont, Stillwood offers two welcoming homes just 5 miles from Woodstock — where open skies, forest paths, and quiet, star-filled nights set the tone.

A PLACE TO TRULY UNWIND

Tucked along a quiet country road in the Green Mountains, Stillwood offers space to spread out, explore, and settle in.

Evenings are shaped by star-filled skies and the soft hoot of owls. Days begin with light through the trees and trails just beyond your door.

Inside, each home feels warm and inviting — comfortable beds, modern essentials, fast Wi-Fi, and thoughtful touches throughout. Outside, rolling hills and wooded paths invite you to wander at your own pace.

It’s the kind of place where you arrive… and exhale.

This place was so nice. We had such a nice time hiking right out the back door and enjoying the area. So close to town and skiing, it was perfect. The space was really great for our family, we enjoyed cooking in the kitchen and the family room for reading by the fire.

I LOVED staying here!!! Lulu’s cottage was so cute. The place was very clean and decorated so nicely. The kitchen was stocked with everything you need. The cottage is so quiet and peaceful and the views are beautiful. Lulu was very communicative and so kind. Her dogs are so super sweet. This place is truly magical and I will definitely be back again!

THE PROPERTIES

These two charming homes sit on 18 peaceful acres in a quiet country setting, surrounded by open space and forested trails. Both feature high-speed internet, dedicated workspaces, a fire pit, hammock, and BBQ for relaxing indoors or out.

The cozy two-story cottage  offers 2 bedrooms, 1 bathroom, and beautiful views of the pasture and hillside — perfect for couples or a small family.

The spacious single-story home (1,900 sq ft) includes 3 bedrooms, 2 bathrooms, a chef’s kitchen, and a large private yard — ideal for families or groups.

Traveling with a larger group? Book both the cottage and the house together for extra space and privacy.

THE LOCATION

These vacation homes are ideally located between Hartland and Woodstock, Vermont, just 10 mins from Woodstock, GMHA, Brownsville, I-91 Exit 9, and Ascutney Mountain.

A short drive brings you to the best of the Upper Valley, including Dartmouth College, Quechee Gorge & Ski Hill, and the Saskadena Six ski area.

Outdoor enthusiasts can step directly onto the VAST trail system or explore the woods right from your doorstep. In winter, enjoy snowshoeing on the property’s trails — we provide three pairs of snowshoes — or take advantage of the sloped pasture for some classic Vermont tubing fun. Summer and fall bring hiking, cycling, and peaceful walks along Densmore Hill Road.

Lulu's place is something that I think is somewhat rare on Airbnb these days - it feels like a home. I really appreciated the fully stocked kitchen and the detailed local recommendations (including hikes and scenic drives). Waking up in that space was so peaceful - exactly what I was looking for in a weekend to Vermont. I felt like I could've stayed forever.  I've spent a lot of time in the Woodstock area, and this is as good as it gets without having to spend down your savings account.

This was by far my favorite air bnb stay. The place was very clean, bed was comfy, kitchen was well equipped, views are outstanding. The house smelled so good too! Lulu is so sweet and welcoming. She made sure we had everything we needed. She had a super helpful welcome book with suggestions of food places, bars, and walking trails. We stayed with our dog and he loved playing with her two dogs.  We can not wait to stay here again.

Features & amenities at Stillwood,Vermont

At a glance...

Coffee...of course

Nothing spoils a vacation like bad coffee can. No Keurigs here! Each home is equipped with a french press & coffee grinder, percolator, and drip machine. The main house also has a Chemex pour-over. Stonewall organic dark coffee, half & half,  sugar, and a few teas to choose from are provided.

Helpful but unintrusive host

I take guest privacy seriously. The dogs, unfortunately, did not get that memo. I live in the barn at the very end of the property, so you won’t see me unless you need something; the dogs, however, may wander by for a friendly sniff. The house and cottage each have their own separate areas, so you won’t run into other guests unless you go looking for them.

Lovely walks & hikes

Walk up or down Densmore Hill Rd with it's babbling brook to keep you company, or go for a wander in the local fields and woods right from the property. There's some fabulous dog-friendly hikes which are also very close by. Click here to see a collection of local dog-friendly hikes.

Fios internet

We are very lucky to have fast FIOS (fiber-optic) internet here. While cellular/tower access might be spotty, you can use the wifi for everything you need, including wifi-calling.

Extra Services

Want the fridge stocked? Decorations for a special occasion? Your dogs cared for? A massage? A tent set-up for the kids? A chef? Something else? Just put a note in your booking or email me to discuss.

Star gazing (& telescope)

With zero light pollution, the star-gazing here is nothing short of spectacular. There's a Zhumell Z10 Deluxe Dobsonian Reflector Telescope in the main house for folks who want to get a closer look at the planets.

Peaceful & private setting

Located on 18 acres, flanked by woods and the adjacent Densmore Hill; rarely do you hear any man-made noise. Many describe this spot as "an oasis." With a view of the adjacent hill, this is also a great spot to see the fall colors.

Outdoor dining

Both the cottage and the house come equipped with a modern propane BBQ, outdoor seating, hammocks, and a fire-pit. Dine al-fresco under the stars!

Friendly animals

My two friendly sheep (Rambo & Rocky) are frequently grazing in the pasture, and my two dogs (JoJo & Brindle) get along well with people and other friendly dogs.

Unpretentious

The homes are designed to feel relaxed and welcoming, not staged. Expect plants, art on the walls, books and games, layered textiles, and thoughtful touches throughout.



In the kitchen, you’ll find well-stocked essentials — coffee, tea, herbs and spices, quality cookware, sharp knives, and bakeware — so settling in feels easy.

Things to do

From wonderful restaurants, kid-friendly activities, dog-friendly spots, skiing & snow-shoeing, baking classes at King Arthur, farmers markets, hiking, biking, swimming holes, kayaking (two kayaks & one SUP provided), art galleries, theatre, old time country stores, float tanks, and lots more - there's plenty to do whether rain or shine. View Things to Do.

Bird Nerds

Birdlife is everywhere at Stillwood. Early mornings bring songbirds moving through the trees, woodpeckers drumming in the distance, and the occasional hawk circling overhead. As night settles in, the soft hoot of owls carries across the hills.

Absolutely the best Airbnb we’ve stayed in. Lulu’s place was spotless and had the nicest touches. A snack and drink basket, peaches from the peach tree outside, excellent coffee, cream in the fridge, great bedding, cozy bedrooms…. I could go on and on. We were in town for a horse show and wish we had had more time to really enjoy this space. We brought our two dogs with us and there were some great areas to walk them, and even a dog bed and a few dog toys. There literally wasn’t anything we didn’t like about this stay. We will definitely be back!!!

We absolutely loved our stay here! The home was spotless, beautifully decorated, and had that perfect blend of cozy charm and modern comfort. The beds were super comfortable, and the kitchen had everything we needed for a relaxing weekend in. The location couldn’t have been better, being approximately 15 minutes from the center of Woodstock with great coffee shops, restaurants, and little boutiques. We also loved exploring the nearby trails recommended by our host, Lulu. Lulu was incredibly welcoming and responsive from start to finish, offering fantastic local recommendations and checking in to make sure everything was perfect. I’d come back here in a heartbeat—whether for a quiet retreat or a base to explore all that the area has to offer. Highly recommend!

ABOUT

Lou (or Lulu)

Hi! I grew up on a small farm in England, where life was muddy, simple, and full of animals. In my twenties I came to the US on a whim and a bit of a wild adventure, and somehow it turned into home. After 13 years in the software world in Santa Barbara, I felt the pull back to the countryside and moved to Hartland, Vermont in 2007.

These days I split my time between a small gardening business, business consulting, and caring for these two vacation rentals. I’m happiest with my hands in the soil, tending to my animals, or making these spaces feel warm, welcoming, and truly “home;" the kind of place I always wished for when I traveled. I hope you’ll feel that same ease and comfort during your stay in Vermont.

A truly New England experience with delightful old England touches. A perfect location between the facilities of Hanover and Woodstock and the quietness of the woods. We were tracing the places so special to Robert Frost and inspirations for his poetry, and this was a cosy home base to which we were delighted to return after our day trips. Lulu was so kind and welcoming, but gave us space to enjoy a special trip together. All mod cons with TV and wifi but just eating and cooking together, reading and appreciating the landscape were our greatest pleasures. We didn't bring a dog but appreciated the consideration offered for furry friends. Thank you, Lulu, for a very special experience.

CONTACT

Send me an email and I’ll get back to you within a day, or text me at 603.322.0647.