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 spacious living area features modern seating arrangements with natural light streaming through large glass windows. A small table is set by the window, overlooking the garden. Polished wooden floors and decorative items add warmth to the inviting atmosphere.
Guest house in Marlboro Township
4.97 out of 5 average rating, 181 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!

Top guest favourite
The entryway features a welcoming entrance with a wooden door, adorned with a green wreath. A glimpse into the bright interior reveals modern seating and natural light streaming through large windows, enhancing the inviting space that awaits inside.
Chalet in Wilmington
4.97 out of 5 average rating, 138 reviews

Snug Chalet - Wi-Fi + Close to Mount Snow

This stylish 1971 chalet is a country retreat with modern comforts for you and your family... complete with strong WiFi and a fenced-in dog yard! The minimal cabin is tucked in the trees and set up for families and friends, pet & kid-friendly. 10-15 Minutes to Mount Snow 10-15 Minutes to Downtown Wilmington This is a country house, not a boutique hotel :) If booking during winter or spring months, we HIGHLY recommend a 4wd vehicle as the weather can cause some tough road conditions (snow/mud).

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.

Guest favourite
A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.
Home in Guilford
4.95 out of 5 average rating, 132 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!

Top guest favourite
A cozy tiny cabin, constructed with wooden beams and a sloped roof, is situated among tall trees. The porch features a railing, inviting seating, and a lantern. Sunlight filters through the foliage, casting a soft glow on the forest floor covered in pine needles.
Treehouse in Brookline
4.98 out of 5 average rating, 257 reviews

Glamping Cabin with Hot Tub on Flower Farm

<b>Vermont's Most Wish Listed</b> ﹏﹏﹏ Nestled in a wooded grove on Tanglebloom Flower Farm, this unforgettable glamping-inspired farm stay invites you to escape the everyday & immerse yourself in nature - comfortably. Designed with a clear roof looking up to the trees and screened sides to let in the breeze, the handmade tiny cabin invites you to slow down. Explore southern Vermont's hikes, farmer's markets & swimming holes or stay put. Perfect for a romantic couples retreat or solo getaway.

Guest favourite
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
4.93 out of 5 average rating, 103 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.

Top guest favourite
Tiny home in Chester
4.99 out of 5 average rating, 103 reviews

Tiny A-Frame Rest House in Woods near Mountains

Newly built A-Frame getaway cabin built in the middle of the woods of Vermont. Unplug from it all at this special space surrounded by nature. Enjoy doing yoga and relaxing on the deck, remote working with fiber optic wifi, utilizing the fire pit to roast smores, or taking a walk around the walking paths on the property! There are also nearby hikes, swimming spots, skiing destinations, and drinking/eating spots! We are 35-40 minutes from Stratton, Mount Snow, Bromley, Okemo, and Magic Mountain!

Top guest favourite
Tiny home in Wilmington
4.99 out of 5 average rating, 366 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, 307 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, 213 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
4.97 out of 5 average rating, 157 reviews

Private Brook Chalet: Hot Tub, Fire pit, Mt. Snow

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

Top guest favourite
A gently sloping lawn leads up to the light-colored building, framed by lush gardens and vibrant greenery. A pair of purple Adirondack chairs sits invitingly on the grass, offering a serene spot to enjoy the surrounding landscape.
Flat in Marlboro Township
4.93 out of 5 average rating, 296 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.

Popular amenities for Dover holiday rentals

When is the best time to visit Dover?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price₹40,888₹43,060₹31,256₹22,758₹21,624₹20,113₹21,719₹21,719₹22,758₹24,174₹23,985₹37,111
Avg. temp-5°C-4°C1°C8°C14°C18°C21°C20°C16°C9°C4°C-2°C

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Dover?

    Dover has more than 530 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in chalet rentals in Dover?

    Experience the best of Dover with our chalet rentals, starting at about $100 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 Dover?

    Four-legged friends are welcome in Dover. Choose from more than 150 vacation rentals for guests traveling with pets.

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

    Yes! Work meets play with ease at over 260 vacation rentals in Dover featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Dover vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 220 vacation homes with pools in Dover, available on Airbnb. Make a splash and soak up the sun in style!

  • Do boutique hotel rentals in Dover have air conditioning?

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

  • Do cabin rentals in Dover have a kitchen?

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

  • Do condo rentals in Dover have wifi?

    Absolutely! We offer over 130 condo rentals with wifi in Dover. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Dover have free parking?

    Absolutely! We offer over 220 house rentals with free parking in Dover. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Chalet Rentals in Dover?

    Enhance your stay in our Chalet Rentals with the most popular amenities: over 50 homes with free parking, over 50 homes with a kitchen, over 20 homes with air conditioning, over 50 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

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 ₹4,721 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!

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