Holiday houses in Bridgewater

4.99 out of 5 average rating, 147 reviews

Home in Barnard

The Looking Glass, a modernistic escape

Welcome to The Looking Glass, a modernistic escape located in Barnard, Vermont! With floor to ceiling, south facing windows, you’ll be relaxing in comfort while taking in breathtaking views of the Green Mountains! You’ll love our commercial grade kitchen, boasting high-end cookware, a Wolf range and Subzero fridge. Take the spiral staircase upstairs to enjoy a long bath before calling it a night in the spacious king bed. Explore Silver Lake & Woodstock! Hike, bike or ski the neighboring trails

4.98 out of 5 average rating, 196 reviews

Cabin in Woodstock

Cozy Log Cabin, Peaceful Retreat, 1p Late Checkout

Cozy Cabin doesn’t charge an additional cleaning fee and offers a late 1pm checkout to our guests! We focus on a comfortable, relaxed, Vermont experience. If you’re looking for a peaceful, yet accessible location, we are situated on 15 acres located between Woodstock Village & Killington. There’s fiber WiFi, Hulu with Starz, MAX, +Live TV w/local channels, ESPN+, Disney+. Also Amazon movies & music, Netflix & Peacock. The Rec Room has a pool table, darts, lounge, gym and a desk for remote work.

4.98 out of 5 average rating, 105 reviews

Chalet in Woodstock

Falcon House: VT Chalet w/Sauna, Bike to Village

Welcome to Falcon House! A modern VT chalet w/sauna at the edge of a 60 acre forest ∙ Outdoor Finnish sauna, shower, yoga platform & hiking trails ∙ 5 min to Woodstock village, 20 min to ski Killington ∙ Spotlessly clean, tastefully furnished, well stocked with thoughtful amenities ∙2 bedrooms, 2 full baths. Lofted king master has ensuite +Lower level den w/double futon ∙ Chefs kitchen, fireplace, 2 TVs & WiFi ∙ Brookside deck w/BBQ & dining ∙Follow Falcon House on Social @falcon_house_vt

4.97 out of 5 average rating, 222 reviews

Cottage in Bridgewater

Newly Renovated, Hot tub, 2min to Killington lift

Stone’s Throw Vermont is a 3 bed/1.5 bath cottage with hot tub, fireplace, and space for 6 guests conveniently located in central Vermont. Placed right on the US-4 corridor; you’re 2 minutes from the Killington Ski Resort’s Skyship Ski Gondola escorting you to the world class amenities of Killington Resort, 5 min from the best craft beer in the region at Long Trail Brewery, 10 min to Echo Lake, and 20 min from the shops and cafes of Woodstock, VT. Truly everything is a Stone’s Throw away.

Superhost

Cabin in Bridgewater

4.91 out of 5 average rating, 100 reviews

100 Acres Views & Creek near Woodstock/Killington

You will leave the demands of your busy lifestyle behind when you vacation on our 100+ acre 4 BR 2 BA cabin property with a babbling crystal clear mountain creek. Place your beach chair in the creek, relax with your favorite book for Best Spa Experience Ever! Large open covered porch with porch swing seating to enjoy the expansive mountain views, listen to the leaves rustle and the stream running in the distance. Miles of hiking & biking trails, skiing, restaurants and more nearby.

Guesthouse in Wallingford

4.98 out of 5 average rating, 699 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Comfortable guesthouse located conveniently on US Route 7 near ski areas. Half hour from Manchester Outlet Stores. Near Long Trail/Appalachian Trail, Weston and Dorset Playhouses and miles of scenic country roads. Close to Elfin Lake and White Rocks National Recreation Area.Great for couples, small families, solo adventurers, and business travelers. Queen size bed and full kitchen. Great for overnight stay or week-long vacation to enjoy the beauty of Vermont. No cleaning fees!

4.97 out of 5 average rating, 395 reviews

Cottage in Windsor

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

5 out of 5 average rating, 258 reviews

Barn in Woodstock

THE LOFT, stunning views from a timber framed barn

Welcome to "The Loft". The loft is a newly built apartment on the top floor of a timber framed barn. The owners are designer/builders who have combined the elements of old world craftsmanship with high tech efficiency to create a living space that is bright, airy and yet cozy. Powered by solar, this attached carriage barn is located on a quiet back road 3.5 miles from Woodstock Village and 3 miles from GMHA. The Loft has its own private entrance, parking and a sunset balcony.

Superhost

4.86 out of 5 average rating, 128 reviews

Blueberry Hill Escape | Pet Friendly | HotTub | Fi

Welcome to Blueberry Hill Escape - Discover year-round fun from skiing, mountain biking, hiking, leaf peeping, and more. Just 12 minutes from the Killington Skyeship Base Lodge, 16 minutes to Woodstock, and 20 minutes to Okemo. A 1,560 sq foot home with a large open floor plan, a master ensuite with 1 Cali King-sized bed, a second bedroom with a Queen-sized bed, and a 3rd bedroom outfitted with a twin-over-full bunk bed and twin trundle bed, this home comfortably sleeps 8.

4.98 out of 5 average rating, 243 reviews

Guesthouse in Woodstock

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED.

4.87 out of 5 average rating, 106 reviews

Apartment in Bridgewater

Skyeship Woods - 7 Beds + Hot Tub

Welcome to your private getaway in the middle of Vermont’s most active recreational region. Skiing, mountain biking, hiking, fly fishing, equestrian sports – it’s all just minutes away! This spacious four-bedroom, two-bathroom apartment sleeps 12 and a private hot tub. It is set on a quiet, wooded hillside conveniently located directly off Route 4 and only one mile from the Killington Skyeship Gondola, which transports you to the main mountain.

4.96 out of 5 average rating, 610 reviews

Apartment in Rutland

Your home away from home

Another glorious time of year in Vermont! Our house is close to the mountains (Killington, Pico, Okemo). You'll love our space for its central location to lakes, hiking, skiing, golf, restaurants and dining, downtown, art and culture, shopping and medical facilities.This first floor apartment with its home-like atmosphere has a separate entrance. It is good for couples, small families, solo adventurers, and business travelers.

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Other great holiday rentals in Bridgewater

5 out of 5 average rating, 14 reviews

Stunning Mountainside Escape on 5 Acres w/ Hot Tub

HillaryRating, 5 stars4 months ago

Perfect house and location for a ski group of 10. Beautiful house, plenty of space, and the hot tub was exactly what we needed to relax. Very close to Long Trail Brewery, great spot for food and drinks. About 15 min drive from the closest Killington lodge, about 20-25 mins from K1. Alyssa was very responsive and helpful from booking through the stay. Highly recommend!

4.94 out of 5 average rating, 18 reviews

Quaint Cottage

DaliaRating, 5 stars3 months ago

David was very friendly and responsive. We enjoyed the location and the peaceful atmosphere. I was with my sister. The stay was a great experience and felt well worth it. Just a note—one bedroom is accessed via a spiral staircase, another by a ladder, and there’s a sleeper couch in the living room. Would definitely recommend!

4.98 out of 5 average rating, 50 reviews

Cottage in Bridgewater

Riverside Cottage - Bridgewater Vermont

ChelseaRating, 5 stars2 days ago

Great stay, hosts were both very responsive during our entire stay. Location and surroundings are beautiful. Game room was a hit!

4.98 out of 5 average rating, 51 reviews

Cabin in Bridgewater

500 Acre Farm Retreat: OQ Farm's Priory

KeriRating, 5 stars1 month ago

If you are aiming to book an experience, more than just a traditional stay, do not hesitate and book now! We traveled to OQ Farm with our three daughters (my 8 year-olds request!) and it was an incredible experience being part of the farm and exploring the property. Accommodations were spacious, clean and well appointed. The hosts (and children) are approachable, kind and felt being amongst old friends! There were tears as we left. We have already recommended OQ Farm to family and friends. And our daughters are planning their return to the farm! Unforgettable!

5 out of 5 average rating, 13 reviews

Apartment in Killington

New Resort Condo Close to Lifts

DevinRating, 5 stars1 month ago

We had a great stay here. It has everything you need in a decent sized charming space. Would highly recommend.

4.98 out of 5 average rating, 57 reviews

Secluded/Hot Tub/views! Minutes to Everything!

AndreaRating, 5 stars1 month ago

The space was just as described. The view of the mountains is beautiful, and the house sits far enough above the road that there's no sounds of traffic. It felt secluded and peaceful, with all the amenities one would need.

4.94 out of 5 average rating, 36 reviews

3BR Farmhouse-Long Trail Brewery

CaitlinRating, 5 stars1 month ago

Rich's house was perfect for our stay! Everything was just as shown, very comfortable and great for our family. I got fast responses whenever I had questions and we loved the proximity to Long Trail!