Holiday rentals in Dover

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Top-rated holiday rentals in Dover

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

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Top guest favourite
A stone patio area with a dining table and chairs invites relaxation outdoors. The guesthouse features large windows that provide views of the surrounding woodland. Lush greenery and natural light create a serene setting, complemented by a nearby path leading to the garden.
Guest house in Marlboro Township
4.97 out of 5 average rating, 182 reviews

Refined, serene and like no other, Marlboro, VT.

Our elegant, supremely comfortable, and private guesthouse is surrounded by a wonderful garden and 350 acres of woodland in the quiet of rural Vermont. We are 30 minutes from Brattleboro to the east, with its many shops and restaurants, and 12 minutes from the small town of Wilmington to our west, with some restaurants, shops, and a supermarket However, we always recommend bringing groceries, etc., for your first night and next morning. We are pleased to offer a 20% discount for 7 days or more!

Guest favourite
An open-concept living area features a dining table set for six, with a gas fireplace framed by a white brick mantel. A television is positioned on a stand nearby, with comfortable seating arranged around the room. Natural light filters in through adjacent windows.
Home in Dover
4.9 out of 5 average rating, 122 reviews

Private Hot Tub, 2 Min to Mt Snow, Cozy Fireplace!

Available all year, only 2 min from Mt Snow! Open concept living with bar counter overlooking a dining area with fireplace and TV lounge. New window AC units available from Memorial Weekend to Labor Day in 1st Bedroom and Living Room/Kitchen. New outdoor hot tub in the backyard! BB charcoal grill available in summer months. Fully equipped kitchen and linens provided. Essentials as a starter kit provided for the first couple days. One pet allowed but must be disclosed at reservation (fee applies)

Guest favourite
Home in Guilford
4.94 out of 5 average rating, 137 reviews

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Guest favourite
The custom home features warm wood siding and a welcoming porch with flower boxes. A spacious deck with rustic railings extends from the second floor, while a covered area includes seating. Surrounding greenery enhances the natural setting, creating a serene outdoor ambiance.
Cabin in Wardsboro
4.86 out of 5 average rating, 177 reviews

Mountain side acres

10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

Superhost
A uniquely designed raised container home features multiple levels and large windows that offer expansive views of the surrounding landscape. The structure includes a covered outdoor area below, and the combination of dark wood and metal creates a striking exterior appearance.
Shipping container in Whitingham
4.92 out of 5 average rating, 106 reviews

The House of Pi

Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store will make you fresh egg sandwiches and coffee. Subs or pizza lunch. Welcome to Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views.

Guest favourite
The outdoor pool is surrounded by a chain-link fence and features a concrete deck. Sun lounges and chairs are positioned nearby, with a colorful beach towel draped over a lounge chair. Lush greenery frames the area, providing a serene setting.
Home in Wilmington
4.88 out of 5 average rating, 186 reviews

Adams Farm-"The Little Farmhouse"

A Clean Ranch style home with hardwood floors located on a 100-acre Historic Vermont Farm. Retired farmers live in separate farmhouse & are available throughout your stay. Conveniently located just minutes away from MT Snow Ski Resort, Hermitage Resort, Stratton Mt. for Skiing, Snowboarding, Tubing, Hiking & Mountain Biking. 3 miles from downtown Wilmington. Minutes to public beaches and lakes. Use our trails for snowshoeing, X-Country Skiing or hiking. Our Pool is avail July -Labor day

Top guest favourite
Tiny home in Wilmington
4.99 out of 5 average rating, 377 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Guest favourite
The A-Frame chalet is set amidst vibrant autumn foliage, showcasing a wrap-around deck with wooden railings. A balcony extends above, offering a view of the surrounding trees and an inviting outdoor space with seating.
Chalet in Dover
4.85 out of 5 average rating, 308 reviews

The Mountain A-Frame at Mount Snow

Entire chalet-style A-Frame in Mount Snow with mountain views. Less than 1 mile from the base of Mount Snow and close to all the fun in the Green Mountains: AT access, swimming holes, covered bridges and more! Across the street you can hop on the Moover shuttle that takes you right to the mountain! 2 minute walk to market, coffee shop and local bar. 2 bedrooms + 1 loft, 1 bath, wrap around deck, cooking necessities, Smart TV and WiFi. You can find us on social (tag us!) @themountainaframe

Top guest favourite
The cabin features a wooden exterior surrounded by lush greenery, with large windows allowing natural light to enter. A wooden deck extends from the side, leading to a cozy outdoor area and an adjacent structure, contributing to the rustic charm of the setting.
Tiny home in Dover
5 out of 5 average rating, 215 reviews

Rustic Cabin in foothills of Green Mountains

Rennsli Cabin is off grid + nestled on a forested plateau in the foothills of the Green Mountains. You will feel like you are in the middle of nowhere, unplugged and able to regenerate. Kitchen is equipped with cooking essentials, water, coffee, tea, milk, fresh eggs + homemade soap. It has an indoor compost toilet, outhouse + outdoor shower (May-Oct) Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

Top guest favourite
Chalet in Dover
4.96 out of 5 average rating, 159 reviews

Brook House: Hot Tub, Fire Pit, Ping Pong

The Brook House Vermont is set back in the trees and unbelievably cozy. It's a place to reconnect while listening to the brook. To enjoy big meals, conversations, and games by the fireplace. To bask in the sun or do yoga on the deck, or gaze into dark, starry skies from the hot tub and fire pit at night. There's skiing mins away at Mount Snow, swimming at Harriman Reservoir, as well as hiking, golf, mountain biking, antiquing, breweries, and some of the best food VT has to offer!

Guest favourite
Two purple Adirondack chairs are positioned on a grassy area surrounded by lush greenery, including ferns and flowering plants. The background features a white house nestled among trees, with a stone landscaping accent adding to the natural setting.
Flat in Marlboro Township
4.93 out of 5 average rating, 301 reviews

Shakespeare’s Folly Side Farm and AirBnB.

Located on a gorgeous south-facing hillside in Marlboro, VT, Shakespeare's Folly Side Farm is a light, airy, quiet apartment with stunning views, beautiful gardens, and walking paths. We have friendly a dog, vegetable and flower gardens and a small orchard, with raspberries and blueberries. Free picking in the summer. A magical and inspiring place of rolling lawns and 40 mile views yet so close to the many rich cultural and recreational options in southeast Vermont.

Top guest favourite
A living room features a large stone fireplace with a wood storage basket beside it. A comfortable sofa with decorative pillows faces a wooden coffee table. Natural light floods the space through a large window, complemented by a nearby area rug.
Apartment in Dover
4.88 out of 5 average rating, 261 reviews

Mt Snow Ski In/Out at Seasons

Directly on the mountain. Minutes walk to 2 trails. Full kitchen, dishwater, washer/dryer, microwave. Fireplace with free wood. Large screen TV in living room and tv in each bedroom. Plenty of board games. King size bed in Master. Free parking for 2 cars. Ground floor with deck with tables and chairs for relaxing. Free parking. The pool (indoor & outdoor) and hot tubs are free to renters as is fully equipped gym (all year) and tennis courts in summer.

Popular amenities for Dover holiday rentals

When is the best time to visit Dover?

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Frequently Asked Questions

  • What are the best places to stay in Dover?

    Vacation rentals in Dover include mountain chalets, cabins, and family homes with scenic views. Many stays are found around the slopes or in quieter, wooded neighborhoods.

  • What are the best things to do in Dover with kids?

    Families often explore outdoor adventure parks, go tubing in winter, or visit playgrounds around the area. Nature walks and hands-on workshops frequently suggested for engaging young visitors.

  • What are some of the best things to do in Dover?

    Dover has mountain trails for hiking and biking, scenic spots for photography, and winter slopes for snow sports. Explore local galleries, farm stands, or enjoy seasonal activities around the community.

  • How is the weather in Dover?

    Dover experiences snowy winters around 13–32°F (-11–0°C) and mild, rainy summers near 57–81°F (14–27°C). Fall colors and spring blooms make outdoor exploration appealing, but packing layers for variable conditions is helpful.

  • When is the best time to visit Dover?

    Late summer and autumn are often recommended for scenic foliage and outdoor activities, while winter is popular among snow sports enthusiasts. Spring brings wildflowers and quieter trails throughout the countryside.

  • What are the best places to visit in Dover?

    Dover has mountain recreation areas, local art galleries, and public parks known for seasonal charm. Exploring small shops or visiting surrounding forests are often recommended experiences.

  • What are some hiking trails in Dover?

    Dover has a selection of mountain and forest trails, from gentle paths suitable for families to challenging routes for experienced hikers. Many trails wind through scenic vistas, woodland areas, and wildflower meadows.

  • What are some family activities we can do in Dover?

    Families in Dover often enjoy hiking, sledding, and picnicking at scenic parks, as well as attending craft workshops or local music events. In winter, skiing and snowboarding are frequently suggested activities.

  • What are some of the best day trip ideas from Dover?

    Travelers often explore nearby historic villages, scenic lakes, or local farms for fresh produce and maple treats. Wilderness areas around the region also invite hiking, biking, and wildlife viewing.

  • Are there any pet friendly accommodations available in Dover?

    Many vacation rentals in Dover welcome pets, and hosts often highlight nearby trails and parks for walks. Some properties offer fenced yards or pet amenities for a comfortable stay.

  • What are some local tips for visiting Dover?

    Dress in layers for changing weather, especially if you plan outdoor activities. Explore local markets and roadside stands for Vermont maple products, and check for pop-up events led by area artists.

  • What is Dover known for?

    Dover is known for its mountain scenery, winter sports, and Vermont traditions like maple sugaring. Visitors appreciate outdoor recreation, small town charm, and seasonal festivals.

  • What are the best hidden gems to explore in Dover?

    Dover has locally owned art studios, quiet forest paths, and small lakes that create peaceful corners away from crowds. Explore lesser-known nature spots and roadside farm stands for a more relaxed experience.

  • What are the best foods to try in Dover?

    Dover is known for Vermont-inspired dishes such as maple-glazed treats, local cheeses, and farm-to-table fare. Many eateries highlight homey comfort foods, freshly baked bread, and apple-based desserts.

  • What should I bring for a trip to Dover?

    Pack comfortable layers, waterproof outerwear, and sturdy shoes for outdoor activities in Dover. Bringing swimwear in summer and insulated gear in winter helps you enjoy a range of adventures.

  • What is the nightlife in Dover like?

    Dover has laid-back bars, live music venues, and a handful of restaurants with evening entertainment. Locals often gather for open mic nights or community-focused events.

  • What are the most popular events or festivals in Dover?

    Dover hosts a range of seasonal festivals, including fall harvest celebrations and winter carnivals with snow sports. Summer often brings music concerts, farmers markets, and community parades.

  • Are there family friendly vacation rentals in Dover?

    Dover has a variety of family friendly vacation rentals, including multi-bedroom cabins, chalets, and homes with spacious living areas. Many accommodations feature kitchens and cozy common spaces for group gatherings.

Quick stats about holiday rentals in Dover

  • Total holiday rentals

    Explore 650 holiday rentals in Dover

  • Nightly prices starting at

    Dover holiday rentals start at £37 per night before taxes and fees

  • Verified guest reviews

    Over 20,460 verified reviews to help you choose

  • Family-friendly holiday rentals

    530 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 150 rentals that welcome pets

  • Holiday rentals with a pool

    220 properties feature pools

  • Rentals with dedicated workspaces

    260 properties have a dedicated workspace

  • Wifi availability

    640 of Dover holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Dover rentals

  • 4.8 Average rating

    Dover stays are highly rated by guests – averaging 4.8 out of 5!

Destinations to explore

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  3. Vermont
  4. Windham County
  5. Dover