Vacation rentals in Bridgewater

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Top-rated vacation rentals in Bridgewater

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
A cozy living space features a large window providing natural light. A comfortable couch and chair are positioned around a coffee table. The room includes a spacious bed with a blue and black patterned blanket, while a 50-inch TV is mounted on the wall.
Condo in Killington
4.88 out of 5 average rating, 253 reviews

Killington-Pico ski in/out Studio at base of Pico

At the base of Pico and 10 minutes from Killington. Free shuttle service from my place to Killington. I have a free ski locker and free wood for the fireplace. There is a laundry room with coin operated machines. There is a brand new 50” flat screen tv with cable. It’s a smart tv, that’s hooked up to WiFi, so you can use your Netflix, Amazon or Hulu account if you want. The kitchen is fully equipped. Towels, soap, shampoo and conditioner provided for 1 day. No daily cleaning service. No parties.

Top guest favorite
A living room with a gas fireplace built into a brick facade provides warmth. A comfortable sectional couch faces the fireplace, complemented by a small coffee table. Large sliding glass doors open to a balcony, offering views of greenery outside.
Condo in Killington
4.98 out of 5 average rating, 145 reviews

Cozy Mountain Condo

Updated 1 Bdr Whiffletree condo in the heart of Killington minutes from everything. The condo is fully stocked with all of the essentials you will need for your Vermont get away. Ski locker for all your gear! Sleeps up to 4 with a king bed and queen pullout sofa. Baby Pack & Play crib, mattress and sheets available upon request for $50 per stay. Shuttle in/out service available weekends (Dec–April), or ski home when conditions allow (check Killington trail status). Killington Reg #004858

Top guest favorite
A cozy living area is furnished with a recliner and a sofa adorned with decorative pillows. A small wooden table holds a lamp and a decorative pumpkin. Natural light enters through a curtain-covered window, creating a warm ambiance.
Apartment in Bridgewater
5 out of 5 average rating, 101 reviews

Vermont Retreat

This is a non-smoking one-bedroom apartment with a queen-size bed. It is convenient to mountains, lakes, and more. A great place for a trip skiing, hiking, biking, or kayaking . . Check out our guidebook for many fun places to see and places to enjoy. The apartment has a small kitchen. It has almost anything you would need. Curtis and I live in the yellow house across the driveway and welcome any requests you might have. We are located on a country road that is quiet and enjoyable.

Top guest favorite
The kitchen area features a large island with seating and modern appliances. Natural wood paneling complements the high cathedral ceiling. Glass doors open to a scenic view of the surrounding hills, providing ample natural light and a connection to the outdoors.
Barn in Woodstock
5 out of 5 average rating, 290 reviews

THE LOFT, stunning views from a timber framed barn

Welcome to "The Loft". A lofted space 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. For more go to @theloft.vt

Top guest favorite
The private guest house is surrounded by lush greenery, featuring a covered porch with a chimney and hanging planters. A well-maintained lawn leads to the house, while a backdrop of rolling hills enhances the tranquil setting.
Cottage in Windsor
4.97 out of 5 average rating, 433 reviews

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.

Top guest favorite
A well-appointed bedroom showcases a spacious bed dressed in white linens, complemented by decorative pillows. A wooden bench is situated at the foot of the bed. A large mirror and artful wall decor enhance the serene atmosphere, while natural light enters through a large window.
Home in West Windsor
4.98 out of 5 average rating, 168 reviews

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.

Guest favorite
A spacious hot tub is positioned on a deck, surrounded by trees and offering a view of the distant mountains. Two red chairs accompany the hot tub, creating a relaxing outdoor space. A rustic storage building is visible in the background.
Home in Bridgewater
4.83 out of 5 average rating, 154 reviews

Blueberry Hill Escape | Pet Friendly | HotTub | AC

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.

Top guest favorite
The historic farmhouse features a white exterior with a gabled roof, surrounded by lush greenery. A large tree provides shade in the front yard, and flower gardens can be seen along the stone pathway leading to the porch, which has seating for relaxation.
Apartment in Taftsville
4.8 out of 5 average rating, 189 reviews

Quiet Vermont Farmhouse

Rent a quiet two-bedroom apartment in our 1850's farmhouse in historic Taftsville, Vermont. We are close to the fascinating history, arts, and shopping of Woodstock VT, and near several downhill and cross country ski and snowshoe centers, Marsh-Billings-Rockefeller National Historical Park, and lots of hiking trails, as well as within a short drive of Hanover NH and White River Junction VT. Come enjoy our warm hospitality, wander our gardens, and enjoy our shared patio.

Top guest favorite
A cozy cabin is nestled among the trees, showcasing a rustic wooden exterior with large windows. It overlooks a gentle slope covered in green grass and wild plants, with sunlight filtering through the canopy above, creating a serene and inviting atmosphere.
Guesthouse in Woodstock
4.98 out of 5 average rating, 282 reviews

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.

Top guest favorite
A comfortable living area features a wood fireplace with tools nearby and a mounted television above it. Two armchairs flank a rustic coffee table, creating a cozy space. Large windows allow natural light to fill the room while offering views of the snowy outdoors.
Home in Killington
4.92 out of 5 average rating, 107 reviews

Ski Back to Trail Creek!

Enjoy Killington at competitive pricing without sacrificing comfort! Located in Trail Creek Condo Association. • Ski, hike, bike, or golf just steps away • Cozy up by the wood fireplace (free wood) • Pool, hot tubs, sauna, and game room at community center • 6-minute walk to Snowshed or shuttle (winter weekends/holidays) • Ski home trail (snow-dependent) • Minutes to restaurants, bars, and shops • Convenient bus stop Adventure and relaxation await!

Top guest favorite
A view of the snow-covered path leading to the ski slopes is framed by the C Building’s balconies. Sunlight casts long shadows across the pristine snow, highlighting the tranquil winter scene. The surrounding area is clear and inviting, with ski signage visible in the distance.
Condo in Ludlow
4.93 out of 5 average rating, 160 reviews

Okemo Ski-in/Ski-out, Steps to lift Condo

Just steps of walk to the amazing Okemo slopes, C Building is the closest property to the A-Quad/B-Quad lift and this building offers convenient parking right downstairs and free wi-fi (dedicated Xfinity modem, no issue video conference). You’ll love this cozy place with hardwood floor and private balcony and sunshine after skiing. Great sun exposure. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

Guest favorite
A cozy living area features a brick fireplace with a warm fire. A comfortable sofa adorned with decorative pillows is positioned nearby, accompanied by a wooden coffee table. Wall-mounted art and soft lighting enhance the welcoming ambiance.
Townhouse in Killington
4.96 out of 5 average rating, 133 reviews

Beautiful Spacious Condo at Killington Resort

This cozy and spacious Sunrise Mountain Village condo is perfectly situated to nearby mountain sports at Killington Ski Resort. It welcomes up to eight guests for an unforgettable stay in the Green Mountains! Exceptional access to year round outdoor activities, great community amenities, and a comfortable condo to come home to - what more could you ask for? Book Timberline K4 today for a thrilling Vermont getaway!

Popular amenities for Bridgewater vacation rentals

When is the best time to visit Bridgewater?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$56,054 GYDG$57,923 GYDG$52,525 GYDG$41,314 GYDG$30,311 GYDG$33,217 GYDG$41,729 GYDG$40,691 GYDG$41,522 GYDG$44,221 GYDG$35,501 GYDG$49,203 GYD
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Frequently Asked Questions

  • What are the most popular amenities for House Rentals in Bridgewater?

    Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with air conditioning, over 50 homes with a kitchen, over 50 homes with wifi, over 50 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there vacation rentals with a dedicated workspace in Bridgewater?

    Yes! Work meets play with ease at over 70 vacation rentals in Bridgewater featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do cabin rentals in Bridgewater have wifi?

    Absolutely! We offer over 10 cabin rentals with wifi in Bridgewater. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Bridgewater?

    Bridgewater has more than 90 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there Bridgewater vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Bridgewater, available on Airbnb. Make a splash and soak up the sun in style!

  • Do cabin rentals in Bridgewater have free parking?

    Absolutely! We offer over 10 cabin rentals with free parking in Bridgewater. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Bridgewater?

    Experience the best of Bridgewater with our house rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Bridgewater?

    Four-legged friends are welcome in Bridgewater. Choose from more than 60 vacation rentals for guests traveling with pets.

  • Do cabin rentals in Bridgewater have a kitchen?

    Absolutely! We offer over 10 cabin rentals with a kitchen in Bridgewater. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Bridgewater have air conditioning?

    Absolutely! We offer over 40 house rentals with air conditioning in Bridgewater. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Bridgewater

  • Total vacation rentals

    Explore 160 vacation rentals in Bridgewater

  • Nightly prices starting at

    Bridgewater vacation rentals start at G$18,685 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,830 verified reviews to help you choose

  • Family-friendly vacation rentals

    100 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    150 of Bridgewater vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Bridgewater rentals

  • 4.8 Average rating

    Bridgewater stays are highly rated by guests—averaging 4.8 out of 5!

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windsor County
  5. Bridgewater