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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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
4.85 out of 5 average rating, 159 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.

Top guest favourite
Guest house in North Bennington
4.99 out of 5 average rating, 307 reviews

Birch House - lake, green trees + modern comforts

We're a little guest house near a lake in Vermont with green trees + modern comforts. Perfect for couples + individuals looking to relax + enjoy nature. Renovated, air conditioned space w/ cozy, minimalist vibes. A small modern cabin that's peaceful + private. Tucked into a quiet neighborhood. Main home is a separate building next door. Near Bennington College. 12 minutes to downtown Bennington. IG birchhousevt Please note that due to a severe allergy, it is difficult to accommodate animals

Guest favourite
Apartment in Dover
4.91 out of 5 average rating, 115 reviews

Base of M.S. All Seasons Fun. Deck/HotT/Pool/Sauna

Sunsil Loft @ MountSnow, your ideal Getaway. Walk to the Base. Unbeatable access to skiing, hiking, biking. Vermont never stops to surprise you with its outdoor adventures, great food and views. The loft offers a cozy gas fireplace, private deck. The kitchen has all you need to prep meals. You also have access to the pool (Summer), sauna, hot tub and GYM. Whether you’re skiing, hiking and biking in summer, or enjoying the fall foliage, our loft is your perfect home base in the Green Mountains.

Top guest favourite
Tiny home in Wilmington
4.99 out of 5 average rating, 334 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!

Top guest favourite
A comfortable living area features a dark leather sofa with two accent pillows and a coffee table atop a patterned rug. A dining table with four chairs is positioned nearby, and natural light enters through a window dressed with light curtains. Wall decor includes vintage skis and decorative deer antlers.
Flat in Wilmington
4.92 out of 5 average rating, 144 reviews

Globetrotter Retreat too - Minutes to the Mountain

Newly renovated, fully furnished in heart of quaint mountain village; minutes to Mount Snow, Green Mountains & lakes. Year round outdoor activities: snow sports in winter, watersports/hiking in summer. Quiet 1 bedroom apt on 2nd floor sleeps 4 people in comfort. Private balcony overlooks tranquil woods & rolling river. Steps to restaurants, bars & shopping. Supermarket is a short walk. Free Moover bus stop across the street ride for free to local destinations! 18 years or older guests only.

Top guest favourite
The cabin's exterior showcases a warm wooden facade with large, strategically placed windows. A spacious screened porch extends from the building, inviting natural light and outdoor enjoyment. A stone pathway leads to the entrance, surrounded by landscaped gravel and native vegetation.
Cabin in Jamaica
4.99 out of 5 average rating, 272 reviews

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

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
4.86 out of 5 average rating, 282 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, 203 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+ hosts provide water, coffee, tea, milk, fresh eggs + homemade soap. There is an indoor compostable toilet + outhouse + outdoor shower. Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

Guest favourite
The compact kitchen features modern appliances, including a microwave and refrigerator, paired with wooden cabinetry and a dining area. Light-colored wood flooring extends throughout, and a staircase leads to the sleeping loft above. Decor elements include framed artwork and a vase of flowers positioned on the counter.
Tiny home in Brattleboro
4.85 out of 5 average rating, 219 reviews

Sweet Vermont Tiny Home Get Away

Your unique Vermont retreat is just a click away! Come stay in this custom built tiny house in southern Vermont. We are an easy walk to the train station, art museum, restaurants, shops, and many beautiful nature spots in and around Brattleboro VT, plus a 40 minute drive to the Mount Snow ski area, and local hiking, swimming, boating, skiing, and skating opportunities. A nature lover's paradise! Enjoy the great outdoors and small town living, or cozy up in the tiny house and just relax.

Top guest favourite
A warm living area features high ceilings and wooden beams. A cozy stone fireplace is flanked by large windows, allowing natural light to fill the space. Comfortable seating is arranged around a coffee table, with a view of a wall-mounted TV displaying Netflix.
Chalet in Dover
4.96 out of 5 average rating, 140 reviews

Private Brook Chalet: Hot Tub - Fire pit - Ski

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 spacious great room features a comfortable seating area with a white couch, eclectic armchair, and colorful floor design. Artistic decorations are placed on the walls and shelves, with a kitchenette visible in the background. A piano and drums are positioned nearby for guest use.
Guest suite in Wilmington
4.93 out of 5 average rating, 805 reviews

Architectural GuestSuite

The Guest Suite is located on the first floor of an architectural studio in historic Wilmington, Vermont. Please enjoy the piano, drums, and art supplies! The Guest Suite is both UNIVERSALLY ACCESSIBLE, TOBACCO FREE, and ANIMAL FREE due to allergies in our family. LineSync Architecture staff will be working from 8:30am - 5ish upstairs, and once in a while on the weekends. When guests are in we try to be super sensitive and quiet, but footsteps will be heard!

Guest favourite
An open living area features rustic wooden beams and warm lighting. A cozy sofa is positioned near a wood stove, with a small dining table adjacent. The kitchen is visible in the background, showcasing appliances against a backdrop of exposed brick and wood floors.
Cottage in Dover
4.84 out of 5 average rating, 321 reviews

Cozy Camp in Vermont

This cozy camp located in beautiful East Dover, is on a secluded road off the beaten path where the babbling brook can be heard. Close to Mount Snow, Lake Whitingham, Lake Raponda, and only 25 minutes to Brattleboro the adventures are endless! Visit the serenity and beauty of Southern Vermont- especially in Fall during “leaf peeping”. This is a camp-style cottage with rustic charm. Snow tires are a MUST- Nov. - Apr.

Popular amenities for Dover holiday rentals

When is the best time to visit Dover?

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Avg. price£292£306£238£180£171£159£172£172£180£186£197£270
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Frequently Asked Questions

  • 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.

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

    Enhance your stay in our House Rentals with the most popular amenities: over 120 homes with a bbq area, over 80 homes with air conditioning, over 210 homes with wifi, over 30 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • 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.

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

    Experience the best of Dover with our condo rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget 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 200 vacation homes with pools in Dover, available on Airbnb. Make a splash and soak up the sun in style!

  • 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.

  • Do chalet rentals in Dover have a bbq area?

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

  • Do townhouse rentals in Dover have a gym?

    Absolutely! We offer over 30 townhouse rentals with a gym in Dover. Enjoy a tailored experience with all the comforts you desire.

  • Do townhouse rentals in Dover have wifi?

    Absolutely! We offer over 80 townhouse rentals with wifi in Dover. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Dover?

    Dover has more than 480 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about holiday rentals in Dover

  • Total holiday rentals

    Explore 610 holiday rentals in Dover

  • Nightly prices starting at

    Dover holiday rentals start at £22 per night before taxes and fees

  • Verified guest reviews

    Over 18,420 verified reviews to help you choose

  • Family-friendly holiday rentals

    480 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 150 rentals that welcome pets

  • Holiday rentals with a pool

    200 properties feature pools

  • Rentals with dedicated workspaces

    260 properties have a dedicated workspace

  • Wifi availability

    590 of Dover holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Dover rentals

  • 4.9 Average rating

    Dover stays are highly rated by guests – averaging 4.9 out of 5!

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windham County
  5. Dover