Holiday rentals in Charlestown

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Top-rated holiday rentals in Charlestown

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Guest favourite

Flat in Springfield

4.91 out of 5 average rating, 223 reviews

Farm Barn apt. 3 bedr, 2 bath, fiberoptic internet

Getaway for families, couples or groups. Apt. in our Barn. High speed internet, so ideal for "work from home". Full kitchen with oven, microwave, dishwasher, big fridge , 3 bedrooms, 2 baths, Dining/Living room with TV ( Antenna, no cable, Roku: bring your passwords for Netflix..) Fields, forest, hill and river on our property. We allow one friendly dog at a time but it is not allowed to stay in the apt. by itself (daycare in Spgf avbl). Please add the dog to your booking for the one time 35 $.

16–23 Jun

$139 SGD per night

Guest favourite

Cabin in Bradford

4.98 out of 5 average rating, 334 reviews

Deer Valley Retreat, Lovely Log Cabin

This Lake Sunapee Region cabin retreat is perfect for romantics, artists, writers, outdoor enthusiasts, gardeners, friends, & family. Centrally located between the area's best lakes and mountains, convenient to area attractions, and outdoor activities. Still, the cabin feels like a destination in itself, where you can relax, recharge, and reconnect. Cozy up by the stone fireplace, relax on the porch, see nature, read, listen, play, cook, stargaze, and enjoy just being! M&R license #: 063685

6–13 Jan

$198 SGD per night

Guest favourite

Cabin in Marlow

4.97 out of 5 average rating, 110 reviews

The Birches Cabin, at home in the woods!

The Birches is situated on 10 secluded acres, where guests will enjoy the privacy and scenery the cabin offers. Built in 2020 and designed to accommodate guests. During your stay take a walk on the property, read a book, enjoy a glass a wine, cook a fine meal, and stare at the stars. Centrally between Keene and the Sunapee region, guests have many options on how to enjoy their days such as Skiing, Hiking, Paddling, and Snow tubing. This is a vacation spot, that can be enjoyed all year.

30 Mar – 6 Apr

$173 SGD per night

Guest favourite

Home in Putney

4.94 out of 5 average rating, 339 reviews

Vermont Botanical Studio Apartment

This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

13–20 Nov

$142 SGD per night

Guest favourite

Guest house in Springfield

4.86 out of 5 average rating, 322 reviews

Connecticut River-Cozy Cottage

This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

16–23 Oct

$126 SGD per night

Guest favourite

Flat in Bellows Falls

4.95 out of 5 average rating, 183 reviews

Village Flat with Antique Billiards

Charming and spacious first floor, 3 Bedroom, 1 Full Bath apartment. Sleeps 5 (1 King, 1 Queen and 1 twin). It is nestled in the center of the Bellows Falls village, a short 5-minute walk to downtown, where you will find great little shops and eateries. We are centrally located in Southern Vermont ~ 40 min from several ski areas (Okemo, Magic, Bromley, Stratton, etc.) about one hour from Killington Resort, Mount Snow, and Mount Sunapee (NH), and ~ 20 mins from Brattleboro, VT, or Keene, NH.

23–30 Mar

$214 SGD per night

Guest favourite

Barn in Chester

4.99 out of 5 average rating, 496 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

21–28 Aug

$162 SGD per night

Guest favourite

Flat in Weathersfield

4.99 out of 5 average rating, 157 reviews

The Loft at Weathersfield

Close to Okemo, The Loft at Weathersfield, is just 1/2 hour south of Woodstock / Hanover area and 22 minutes from Okemo Mountain. The Loft, is located in a private agricultural setting with easy access to Vermont's best biking, hiking, fly fishing, skiing, and many equine trails. The loft is 900 square feet with a kitchen/dining room, living room, full bath, one bedroom with a queen bed and one twin bed. There is a spacious deck off the kitchen and a car port underneath.

24–31 Dec

$169 SGD per night

Guest favourite

Cottage in Windsor

4.97 out of 5 average rating, 320 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.

10–17 Nov

$186 SGD per night

Guest favourite

Loft in Sunapee

4.97 out of 5 average rating, 468 reviews

Lake Sunapee Harbor Cozy Retreat

In the heart of Sunapee Harbor is “Topside”, a charming suite for guests who want to engage in the active Sunapee life. Topside is perfect for 2 people and comfortable for 3. An efficient use of space offers a queen-sized bed, pull out love seat couch, kitchenette stocked with snacks and basic cooking needs, private bathroom, Wi-Fi, Smart TV, board games, and your own tree-top deck. Very clean, stylish, and comfortable!

24–31 Jan

$166 SGD per night

Guest favourite

Flat in Weathersfield

4.97 out of 5 average rating, 110 reviews

Cute VT Bungalow With 180 Degree View of NH

Located on a quiet country dirt road you will find this cozy apartment perfect for a weekend getaway. A short walk and you will be amazed at the 360 degree views of Vermont and New Hampshire. Centrally located near Okemo, Sunapee and Killington mountains, ski all 3 mountains in a weekend. Explore covered bridges, walking trails, scenic bike rides, or tubing on the Connecticut River.

27 Nov – 4 Dec

$244 SGD per night

Guest favourite

Flat in Claremont

4.88 out of 5 average rating, 111 reviews

Beautiful 1 bedroom apartment with balcony

Bienvenue chez nous! Experience comfort and modern beauty in this completely renovated apartment attached to a historic Victorian home. The one bedroom apartment has a private bathroom and your own balcony to enjoy. Close to popular skiing areas of Mt Sunapee (20 minutes) and Okemo (35 minutes), in addition to enjoying local hiking and cycling at Mt Ascutney, Moody Park, and Arrowhead.

22–29 Oct

$120 SGD per night