A quintessential New England town known for its historic buildings, scenic farms, exquisite valleys, and radiant fall foliage, Woodstock is a leaf-peeper’s sanctuary. It is an ideal getaway for those who want to escape crowds and have a laid-back vacation.
Hike the picturesque trails that run through Billings-Rockefeller National Historical Park, sample delectable cheeses at Sugarbush Farm, throw stones in Ottauquechee River, indulge in breathtaking scenery at the Simon Pearce, go picnicking on Mount Peg, and explore local shops and historic buildings downtown.
From Victorian B&Bs to cozy cottages to boutique hotels, there are plenty of unique accommodation options in Woodstock. Here are the top cool and unusual hotels in Woodstock, Vermont (in no particular order)...
1. Woodstock Inn & Resort – a bright, upscale and Instagrammable hotel featuring a spa and wellness center
A high-end resort nestled amidst landscaped grounds and groves, about four miles from Suicide Six Ski Area.
Quaint rooms at Woodstock Inn & Resort come equipped with private bathrooms, mini-fridges, Keurig coffee makers, iPod docks, flat-screen TVs, and free Wi-Fi. Upgraded units feature private porches and fireplaces.
Valet parking and a shuttle service to the ski area are complimentary for all guests staying here. The 4-star hotel also boasts a casual restaurant, a tavern, a clubhouse grill eatery, a fitness center, a golf course, tennis courts, a spa, indoor and outdoor pools, a sauna, and a steam room.
Address: 14 The Green, Woodstock, VT 05091, United States
- To book, check prices or availability for Woodstock Inn & Resort
2. 506 On the River Inn Woodstock – a stylish, elegant and unique accommodation where guests can enjoy panoramic views of the river and gardens
If you want to stay steps from the stunning Ottauquechee River, there is no place better than this high-end boutique hotel. Boasting elegant rooms and suites, 506 On the River Inn Woodstock combines country charm with big city amenities. The vintage-chic decor and balconies with breathtaking river views will make you want to stay in your room all day long.
Each room at the 4-star hotel comes equipped with microwaves, mini-fridges, coffee makers, flat-screen TVs, and rocking chairs on the patio. While living here, you’ll also have many free perks including breakfast, parking, and evening snacks.
With an onsite bistro, a cozy lounge, and a vintage-style bar, this boutique hotel in Woodstock will keep you from leaving the hotel even during the day.
Address: 1653 W Woodstock Rd, Woodstock, VT 05091, United States
- To book, check prices or availability for 506 On the River Inn Woodstock
3. The Woodstocker B&B – an award-winning, rustic-chic and cool accommodation located in the heart of Woodstock
The Woodstocker B&B is yet another stylish B&B steps from Ottauquechee River. Guests sojourn in uniquely designed rooms and suites with pillow menus, private bathrooms, flat-screen TVs, MP3 players, and complimentary Wi-Fi.
The communal kitchen has a sophisticated dining area where made-to-order breakfast is served. You can order snacks for free all day long. You’ll also have access to an onsite library and a garden.
Address: 61 River St, Woodstock, VT 05091, United States
- To book, check prices or availability for The Woodstocker B&B
4. The Lincoln Inn & Restaurant At The Covered Bridge – an elegant, cozy and unique accommodation well known for being a culinary gem
With a classy onsite eatery and plush rooms, The Lincoln Inn & Restaurant At The Covered Bridge is arguably one of the best hotels in Woodstock. Guests have three types of accommodation options to choose from, namely a king room, a queen room, and a queen and twin room.
The hotel also features a lush garden, a spacious terrace, a ritzy bar, and a cozy lounge with a fireplace. There are no major attractions within walking distance of this place, but you can enjoy hiking, skiing, and cycling nearby.
Address: 2709 W Woodstock Rd, Woodstock, VT 05091, United States
- To book, check prices or availability for The Lincoln Inn & Restaurant At The Covered Bridge
5. Woodbridge Inn Bed & Breakfast – a historic, stylish and modern accommodation offering guests a complimentary American breakfast every morning
Perched next to Ottauquechee River on West Woodstock Road, Woodbridge Inn Bed & Breakfast features five traditional rooms with antique furnishings and en suite bathrooms. Free Wi-Fi and flat-screen TVs with DVD players are available in all units.
Complimentary amenities include breakfast and afternoon coffee with snacks. All guests have access to a common area with a wood stove and an outdoor area with a fire pit, seating, and impressive mountain views.
Address: 5763 W Woodstock Rd, Woodstock, VT 05091, United States
- To book, check prices or availability for Woodbridge Inn Bed & Breakfast
6. Kedron Valley Inn – one of the most historic accommodations in the Green Mountains where guests can experience a romantic, contemporary and rustic-chic stay
Set in a Federal-style building dating from 1822, Kedron Valley Inn is where you can experience both the quaint ambiance and majestic natural beauty of Woodstock.
Posh rooms at the 3-star hotel have exposed log walls, private bathrooms, and cable TV. Book a two-bedroom suite to have a private terrace and kitchen.
Though there are several great restaurants within a short drive from the hotel, the onsite eatery serves some of the most delicious Vermont classics.
Address: 4778 S Rd, South Woodstock, VT 05071, United States
- To book, check prices or availability for Kedron Valley Inn
7. Jackson House Inn – one of Vermont’s finest accommodations providing guests with a charming, quiet and relaxing stay
Jackson House Inn is a fantastic option for those who want easy access to both the Ottauquechee River and Marsh-Billings-Rockefeller National Historical Park. This upscale B&B is set in a graceful Victorian home located less than two miles from Billings Park and Trails.
With eleven antiques-laden, individually decorated rooms and suites, Jackson House Inn clearly stands out from the crowd. Some units feature canopy or 4-poster beds, whirlpool tubs, and gas fireplaces, while cable TV and Wi-Fi are available in all units.
Onsite amenities include a porch with ample seating, an English-style garden with a maze, a freshwater pond, a porch, and a guest lounge with a fireplace and games.
Address: 43 Senior Ln, Woodstock, VT 05091, United States
- To book, check prices or availability for Jackson House Inn
8. The Village Inn of Woodstock – an upscale, Victorian-inspired boutique accommodation perfect for a couple’s romantic getaway
A stylish B&B sitting across the street from the gorgeous Ottauquechee River, less than a mile from Billing Farm and Museum.
Guests lodge in snug, vintage-style rooms with period furnishings, fireplaces, and 4-poster or canopy beds. Cable TV and complimentary Wi-Fi are available in all rooms, while upgraded rooms also offer 2-person whirlpool tubs.
There’s a formal dining room and a garden terrace where a 3-course breakfast is served for the guests. You can also grab a beer from a cozy onsite bar with stained glass windows.
Address: 41 Pleasant St, Woodstock, VT 05091, United States
- To book, check prices or availability for The Village Inn of Woodstock
9. The Birch Grove – a cozy, quiet and beautiful accommodation in close proximity to popular local attractions
Located on Grove Hill Road in historic Woodstock, this refined B&B offers a quiet retreat amidst lush gardens. There’s absolutely nothing within a mile of this B&B which makes it perfect for those seeking solitude.
At The Birch Grove, you can choose between two types of accommodation, namely a double room or a large twin room. The former is equipped with a double bed and the latter features two single beds.
Address: 76 Grove Hill Rd, Woodstock, VT 05091, United States
- To book, check prices or availability for The Birch Grove
10. The Shire Woodstock – a modern, charming and pet-friendly accommodation with a picturesque river side location
The Shire Woodstock is where you can witness all shades of this gorgeous town, from a laid-back vibe to beautiful views of the Ottauquechee River.
Set in an airy building overlooking the river, this casual hotel is located on Pleasant Street with the Billings Farm and Museum accessible within a 2-minute drive.
Traditional rooms at The Shire Woodstock feature New England-style decor and upscale amenities, including fireplaces, 4-poster beds, whirlpool tubs, flat-screen TVs, and river views. Complimentary perks include parking, morning tea and coffee, and Wi-Fi access. As a guest, you’ll also enjoy access to a riverside seating area and a wraparound porch.
Address: 46 Pleasant St, Woodstock, VT 05091, United States
- To book, check prices or availability for The Shire Woodstock
11. Tentrr – The Perch – a quirky, unique and beautiful accommodation perfect for Millennials and Gen Zs who love the outdoors
This quirky lodging is thoughtfully designed for couples looking for a romantic retreat in the woods. However, it is equally suitable for adventure-seekers who want a camp to retire to after a day full of hiking and exploration.
With a double bunk bed, Tentrr – The Perch can comfortably sleep up to four adults. There’s also a hammock, outdoor furniture, and BBQ grills.
Popular points of interest near the property include Billings Park and Trails and Quechee State Park.
Address: Woodstock, 05071, United States
- To book, check prices or availability for Tentrr – The Perch
12. Sleep Woodstock Motel – a classic, vibrant and 1960’s style accommodation with modern day amenities
Housed in a low-rise building backed by towering trees, Sleep Woodstock Motel provides accommodation in unassuming rooms with flat-screen TVs, microwaves, mini-fridges, Wi-Fi, and Keurig coffee makers. There’s also a two-story, two-bedroom suite featuring a living room with a sofa bed and fireplace.
Located on West Woodstock Road, this low-key motel is steps from Ottauquechee River with Suicide Six Ski Area accessible within a 10-minute drive.
Address: 4324 W Woodstock Rd suite b, Woodstock, VT 05091, United States
- To book, check prices or availability for Sleep Woodstock Motel
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My first true adventure began as a six month voyage around South East Asia as a fresh faced backpacker and ever since I’ve lived a semi nomadic existence, clocking up visits to over 40 countries. I’m a lover of US Road Trips, deserted beaches bathed in warm glow of a sunset, Cuban mojitos, travel destinations far away from the tourist crowds and all things Scandinavian – from cloudberry liquors to Nordic noirs. When not wandering the world and running Global Grasshopper, you’ll find me walking my rescued Greek street dog in leafy South West London, strolling around the Brighton Lanes on random day trips, hunting for photogenic landscapes or daydreaming about my favourite places; Havana, Copenhagen, Italy, Laos, California and the surreally beautiful landscapes of a wintry Iceland.