
House holiday rentals in Woodstock
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Top-rated house rentals in Woodstock
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Epic Views of the Green Mountains
Luxurious bohemian style overlooking one of the most epic views in the Green Mountains. Surrounded by 25,000 acres of National Forest and complete seclusion, yet just a short ride from several towns. Spacious, immaculate, modern home with rustic beams and gorgeous wood floors. Each of the three bedrooms (and baths!) have a wonderful view. The master bedroom is massive and has sweeping views out over the Battell Wilderness and the Long Trail. The front of the cottage is a wall of windows overlooking a beautiful pond and the Green Mountain National Forest. No light pollution. No noise except for the tree frogs and the sound of the White River rushing over the rocks far below in the hollow. It's worth mentioning that Breadloaf Mountain Cottage was a gift that I am grateful for. I still can't believe that I am so lucky to be able to enjoy it frequently. Please understand that those sweeping, epic views you see all around you when you are there, come at a price. Being perched atop a mountain in the wilderness has obvious benefits, but due to frequently changing weather, access and utilties are sometimes a bit more tricky than something in town. Please be prepared to be patient with the weather and the WIFI. While my internet is as good as anywhere in Vermont, it is a rural network and is likely more quirky than urban or suburban utilities. I have a 20mbps service. Breadloaf Mountain Cottage is at the top of a ridge that runs parallel to scenic Route 100. It sits at about 1600 feet above sea level. While completely secluded, it is just 1.3 mile to the Granville Store, and just a few minutes more to Hancock, Rochester and Warren. You could spend weeks just exploring the hiking, biking, swimming and fishing opportunities right from the property! Breadloaf Mountain Cottage is located on Forest Road 55, just off scenic Route 100. While it is easily accessible year round, a 4X4 or AWD vehicle is highly recommended in snow and mud. Quality AT or snow rated tires are a must in the winter. This is true generally in Vermont. Come prepared.

Fresh Snow- Luxury Cabin near Ski Areas
On a cold winter morning Wake up in a luxurious bed in a stylish cabin with panoramic Vermont views. Grab a hot coffee with a book from our library. Hot mug in hand, step out to the porch, look at faraway hills. Make breakfast in the Chefs kitchen. Snowshoe/slide/talk/play with your favorite people/animals in the world. Take a scenic drive to Woodstock, Simon Pearce, Okemo, or the Harpooon Brewery. Kick back with a night around the firepit stargazing Sharing our Red House with you.

Romantic Mountain Getaway
Come enjoy the peacefulness that only living in the mountains can give you, without letting go of every day luxuries. Our place is ideal for romantic getaways with its beautiful and private setting! Lots of things to do in the area as well. The serene Indian Pond is located just down the road and it is ideal for swimming & kayaking in the summer and snowshoeing in the winter. Hike Mt. Moosilauke and enjoy stunning views, or hike Mt. Cube or Smarts Mountain for smaller fun family adventures.

Cozy Bow House Perched in Trees w/ Hot Tub & View
The cozy Bow House is perched up above a lovely valley and boasts large south facing windows, a unique bowed loft and a warm, inviting space to relax. Up a charming dirt road past Brushwood & Fairlee Forests with hiking, biking and ATV trails nearby. Lake Fairlee is a scenic 10 min drive; 15 min to Lake Morey & I-91 and 30 min to Dartmouth College. Enjoy the glow of the rising sun and beautiful views above the fog, unwind in the hot tub surrounded by the magical woods and wildlife of Vermont.

Beautiful Woodstock Home-Perfect for entertaining
Newly renovated - 4 bedroom, 3 bath house, perfect for relaxing or entertaining. Close to all that the Woodstock Village and the Upper Valley has to offer. Amazing location! Only 1.5 mi to the Woodstock Green. Explore the property and feast on the blackberries in summer, raid the tomato garden in the late summer/early fall, and pick the wild fall apples for munching or baking. Bring your snowshoes or cross country skis (in winter) or hiking shoes in summer and explore the property and beyond!

The Willow House: a Modern Vermont Retreat
Just 7 miles (12 minutes ) to the Dartmouth Campus, this newly re-built little house sits beside its own pond on the edge of a sheep pasture. All the comforts of a modern home in 600sqft. Enjoy access to hiking trails and State Forest lands as well as an easy drive to world-class skiing an hour away and all that the Dartmouth College community offers just minutes away. This is the best of pastoral Vermont, with outside living-dining space ( south facing deck and north facing screen porch).

Private Oasis Under 10 Mins from Woodstock
Less than ten minutes from Woodstock Village, this bright, 3 bedroom home is nestled on ten private acres with spectacular views of Pomfret's rolling hills. The open living area features a large picture window, cozy fireplace and fully equipped kitchen. Relax on the spacious deck with dramatic views of Pomfret’s hills. Please read reviews to see what our guests love about staying here: - Beautiful location - Squeaky clean - Fully equipped kitchen - Comfortable beds - Thoughtful amenities

Stunning Okemo Views - 3BD 3BA on 10 Private Acres
Recently constructed on ten private acres with captivating views of Okemo. Three BR, three full bath, air conditioned modern chalet, just 1.5 miles from downtown and 3 miles from Okemo’s base areas. Epic views of Okemo and surrounding mountains from every room. Cozy around the fireplace in the living room or enjoy smores outside by the firepit, or unwind on the deck. Lower level has second living room great for kids with large TV, comfy couches, Pac Man arcade, foosball and board games.

The Spring Hill House
Escape to a haven of natural beauty and tranquility at The Spring Hill House. Our unique bow roof home offers breathtaking views of Camel’s Hump and the majestic Green Mountains, the perfect setting for a rejuvenating getaway. Despite being removed from the hustle and bustle of city life, The Spring Hill House is still centrally located, providing easy access to some of Vermont's most popular destinations. Please note: We have a firm no kids policy due to the open loft and stairs.

Birdie's Nest Guesthouse
Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

Family Escape- rural peace & quiet on a farm
Easy access from the highway! Your cozy, authentic Vermont country stay awaits! We invite you stay in our farmhouse to relax and unwind. We're located only 10 minutes from exit 2 off of 89. Close to Woodstock, Norwich, Lebanon, Dartmouth/Hanover. Enjoy our beautiful valley and our historic farm rich in natural resources. Our farm is well known in the Upper Valley for its round barn, a 10 sided remarkable structure built as a dairy barn in the early 1900's.

Vermont Retreat Near Okemo | 3BR w/ Fireplace
Peaceful 3BR Vermont Estate Near Woodstock & Mt. Ascutney Escape to our serene Vermont retreat on 7 private acres. Just 5 minutes from Mt. Ascutney trails and 15 minutes from Green Mountain Horse Association. Perfect for families, riders, and nature lovers, our modern country home blends comfort with classic Vermont charm. Whether you’re planning a quiet couples’ retreat or a family getaway full of Vermont adventure, you’ll find space, serenity, and style here.
Popular amenities for house rentals in Woodstock
House rentals with a pool

Mountain View Farmhouse w/ Orchard White Christmas

Ski home to Trail Creek!

TheGrizz! Shuttle on/off!

Ranch at Mendon Mt Orchards

Adams Farm-"The Little Farmhouse"

The Brick House on Washington Street

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Historic Home on 17 acres of land. Go escape!
Weekly house rentals

Charming Vermont Schoolhouse

Historic Charm, Located On the River - Rustic Chic

Fabulous Log Home in the Woods

The Barnbrook House

Sky Zen - Ridgeline Retreat

Wright’s Mountain Retreat

Mountain Home ready for you!

Charming, Cozy Cape
Private house rentals

Peaceful Country Getaway 5 Miles from Woodstock VT

Quaint Cottage

New Killington Chalet: Hot Tub, Fireplace, 4Bd2 ba

Secluded Getaway, VT - 15 min from Woodstock

OQ Farm Refectory with Fire Place, Sauna/Hot tub

Relaxing Countryside Oasis!

Scandinavian Serenity Close to Okemo

Dana Road House Sunlit VT Country Home w/HotTub
When is the best time to visit Woodstock?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $578 SGD | $534 SGD | $518 SGD | $611 SGD | $591 SGD | $530 SGD | $450 SGD | $424 SGD | $462 SGD | $578 SGD | $567 SGD | $643 SGD |
| Avg. temp | -7°C | -6°C | 0°C | 7°C | 14°C | 18°C | 21°C | 20°C | 15°C | 9°C | 3°C | -3°C |
Quick stats about house rentals in Woodstock

Total holiday rentals
Explore 70 holiday rentals in Woodstock

Nightly prices starting at
Woodstock holiday rentals start at $141 SGD per night before taxes and fees

Verified guest reviews
Over 1,700 verified reviews to help you choose

Family-friendly holiday rentals
60 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
70 of Woodstock holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Woodstock rentals

4.9 Average rating
Woodstock stays are highly rated by guests – averaging 4.9 out of 5!
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- Okemo Mountain Resort
- Stratton Mountain
- Squam Lake
- Sugarbush Resort
- Stratton Mountain Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Tenney Mountain Resort
- Fort Ticonderoga
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Bromley Mountain Ski Resort
- Dartmouth Skiway
- Whaleback Mountain
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Dorset Field Club
- Hooper Golf Course
- Lucky Bugger Vineyard & Winery
- Autumn Mountain Winery
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Montshire Museum of Science




