Holiday houses in Roxbury

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Top-rated holiday rentals in Roxbury

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Top Guest favourite
A dark cabin is nestled among snow-covered trees, with a thick layer of snow blanketing the ground. The cabin's windows are partially visible, and its roof is capped with fresh snow, creating a serene winter scene amidst falling snowflakes.
Cabin in Royalton
4.99 out of 5 average rating, 253 reviews

Genuine Vermont Sugar House on 70 peaceful acres.

Stay in this genuine Vermont sugarhouse. Our family took great pride in making Maple Syrup and now we take that same pride in sharing this private piece of Vermont with you, our guests. There are trails that will take you through our 70-acre property including the sugar bush we used for the sugarhouse. Relax in the quiet beauty of rural Vermont. Located near the geographical center of VT. We do welcome friendly housebroken dogs. Please see other details under show more. Part of Three Maples LLC.

Guest favourite
A yurt is illuminated softly against a twilight sky, situated amidst trees. The glow from a vent is visible at the top, while warm light spills from an open door, inviting a sense of tranquility in the evening landscape.
Yurt in Randolph
4.94 out of 5 average rating, 466 reviews

Lower Yurt Stay on VT Homestead

We are located in the hills of central VT, close to hiking, skiing and swimming. Disconnect to reconnect! Our homestead is based on permaculture landscape design. Unwind in the traditional Finnish Sauna, relax by the living pool, or kick back in an Adirondack chair looking out at the hills of VT. We have an ideal environment for digital detox. This is one of three listings at our place. We can accommodate groups of six by booking: Lower Yurt Stay on VT homestead and Tiny house on VT homestead

Top Guest favourite
The uniquely shaped house, adorned with shingles, is surrounded by lush greenery. Large windows reflect the vibrant foliage, allowing natural light to illuminate the structure. The natural stone wall complements the rustic aesthetic, creating a harmonious blend with the wooded landscape.
Home in Fairlee
4.96 out of 5 average rating, 568 reviews

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.

Guest favourite
Home in Warren
4.88 out of 5 average rating, 230 reviews

Fiddlehead Greens

Come relax in the quiet woods in the Mad River Valley in this well appointed standalone home. Half a mile walk to Warren Falls and 3.9 miles to Sugarbush Resort. The home is situated on 10 acres offering places to explore and hike in the woods and a fire pit out back. Two minutes from Warren Village and 8 to Waitsfield provide you with dining and shopping close by. This home is well equipped with all you need to enjoy a home cooked meal with a cozy living room to play games and entertain.

Top Guest favourite
A cottage with a wooden exterior is nestled among greenery. A spacious deck with a railing extends from the front, featuring stairs leading down to a natural landscape. Trees surround the property, providing a sense of privacy and tranquility.
Cottage in Hinesburg
4.96 out of 5 average rating, 267 reviews

Bright new cottage in exquisite Vermont setting

Relax in "Findaway" cottage. Centrally located between Burlington and Montpelier and directly adjacent to Sleepy Hollow cross country ski and bike area, Birds of Vermont museum and the Vermont Audubon Center. Settle in and relax, hike right out the door, or sip a drink on the deck overlooking a beaver pond where you may see beaver, otters, deer, birds or even a moose! Surrounded by gardens and not far from downhill skiing and hiking options, swimming, sailing, dining and Lake Champlain.

Top Guest favourite
A secluded cabin is nestled among snow-covered trees, showcasing a timber exterior and large windows that reflect the winter landscape. An inviting deck extends from the cabin, surrounded by a tranquil blanket of snow, creating a serene atmosphere.
Cabin in Roxbury
4.98 out of 5 average rating, 286 reviews

Off Grid Secluded Cabin on 37 Acre Farm

In a secluded, hand-crafted off the grid cabin, come and enjoy the elements with us at Drift Farmstead. A 3-minute walk leads you through gardens and pasture, to Ravenwood, a small, intimate cabin with everything you need. Be it an extended weekend tucked in seclusion, amongst the birds, river and trees, or find the comforts of a 37 acre small farm nestled in the mountains and settle in, working from afar. Top shelf skiing at Sugarbush is near, along with Vermont's finest grub and beer.

Top Guest favourite
A unique bow roof home sits nestled among trees, illuminated warmly against a backdrop of a star-filled night sky. The expansive windows reflect the twinkling stars above, creating a serene atmosphere for stargazing and relaxation.
Home in Starksboro
4.99 out of 5 average rating, 205 reviews

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.

Top Guest favourite
The entrance features a well-maintained pathway leading to a welcoming porch, flanked by vibrant flower beds. The surrounding greenery includes ornamental trees, creating a serene outdoor setting.
Apartment in Williamstown
4.92 out of 5 average rating, 165 reviews

Cozy/Private, close to hospital, i-89

Relax in Central Vermont. Easy access to hike/ski/tour Private apartment, sleeps up to 5, peaceful area, beautiful views, close to VAST trails 5 minutes from I-89, 15 minutes to Norwich University, 50 minutes to burlington, 45 minutes to ski areas, 5 minutes to Rock of Ages, 10 min to Central VT Hosp. Private entrance/bath/living space, deck overlooking trees/mtns/sliding, microwave, fridge, grill, washer dryer, hot plate. Moments to restaurants. 1 queen, twin over full bunk.

Top Guest favourite
A two-story log house is set among trees with snow covering the ground. A wide wooden deck features multiple chairs, and a door is visible on the base level. The structure showcases earthy tones and has a circular window above the entrance, enhancing its rustic appearance.
Home in Roxbury
4.92 out of 5 average rating, 234 reviews

Captain Tom's Cabin - Secluded Vermont Getaway

Welcome to Capt. Tom's Cabin. Nestled in the hills of Vermont with a beautiful view of the Green Mts., this 2-storey, 2 bedroom log house on 44 acres offers seclusion, serenity and privacy. Two large bathrooms, full kitchen, central heat, gas fireplace, pond and deck. Great for winter sports enthusiasts and nature lovers. Good wifi, dog-friendly with a fee. Please google and read Vermont's covid restrictions and agree to adhere to them before making a reservation.

Top Guest favourite
A modern house with wooden exterior is shown from an elevated perspective, surrounded by autumn foliage. A hot tub is positioned on a spacious deck, which includes a seating area with four chairs and a small table. Scenic mountain views and vibrant trees enhance the natural setting.
Tiny home in Warren
4.99 out of 5 average rating, 301 reviews

Luxury Glass Tiny House - Mountain View + Hot Tub

Immerse yourself in nature at Vermont's most unique Airbnb, located in the heart of the Green Mountains. This upscale mirrored glass house was built in Estonia and combines Scandinavian design with jaw-dropping Vermont views for an unforgettable experience. You'll return home feeling rejuvenated after relaxing in a hot tub overlooking Sugarbush Mountain or waking up with a panorama of Blueberry Lake at your feet. *One of Airbnb’s Most Wish-listed Stays of 2023*

Top Guest favourite
A cozy sitting area is seen with a green chair and a gray sofa positioned across from each other on a wooden floor. A round table sits between them, accompanied by a small black side table. A TV is mounted on the wall, and a door with a simple design is visible in the background.
Guest suite in Moretown
4.97 out of 5 average rating, 152 reviews

The Nest Studio

Off a quiet dirt road set up in the mountains, The Nest Studio is a bright and cozy space. Great for couples, the studio has a queen bed with an additional small twin pull out sofa, best for a little one. The newly remodeled Moretown studio is close to skiing, mountain biking, hiking and several wedding venues. Coffee and tea is provided. The Nest has a full kitchen, washer, dryer, and tiled shower. Secure bike storage and bike wash are present on the property

Top Guest favourite
A spacious living area features large windows framing mountain views and a cozy fireplace. Natural wood accents complement the soft furnishings, including a circular glass coffee table atop a patterned area rug. A dining table for two is positioned near the sliding doors leading to the outdoor deck.
Home in Moretown
4.98 out of 5 average rating, 322 reviews

Dramatic Views at the Above the Clouds Guesthouse

As featured in Conde Nast Traveler (1/21/22) Peaceful & impeccable retreat with a 180 degree view of Vermont's tallest mountains. Near Vermont's premier skiing, hiking, & outdoor adventures, you’ll love the sunset views and cozy atmosphere (huge sheepskin in front of the fireplace) and the attention to detail (live-edge wood details, spa-like bathroom). This is an incredible retreat for couples and families, adventurers and business travelers alike!

Popular amenities for Roxbury holiday rentals

When is the best time to visit Roxbury?

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Avg. price$326 NZD$321 NZD$299 NZD$285 NZD$299 NZD$280 NZD$282 NZD$290 NZD$299 NZD$299 NZD$282 NZD$326 NZD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Roxbury?

    Roxbury has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Roxbury with our house rentals, starting at about $130 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 Roxbury?

    Four-legged friends are welcome in Roxbury. Choose from more than 20 vacation rentals for guests traveling with pets.

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

    Yes! Work meets play with ease at over 30 vacation rentals in Roxbury featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Roxbury have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Roxbury. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Roxbury have a kitchen?

    Absolutely! We offer over 20 house rentals with a kitchen in Roxbury. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Roxbury have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Roxbury. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Roxbury have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Roxbury. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Roxbury

  • Total holiday rentals

    Explore 50 holiday rentals in Roxbury

  • Nightly prices starting at

    Roxbury holiday rentals start at $154 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,040 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Roxbury holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Roxbury rentals

  • 4.9 Average rating

    Roxbury stays are highly rated by guests—averaging 4.9 out of 5!

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