Holiday rentals in Bennington

Cozy Comfort on 250 Acre Private Estate

If you’re looking for serenity, peace and quiet, you've found it, amidst a 250 acre private estate. On a lake at the end of a mile long driveway (well plowed in the winter) Is Snowshoe Cabin. Built in 1929 as the garage for "Lakefalls Lodge, it's been completed renovated into a luxurious, cozy home with modern amenities. Guests rave about "views of the snowy pond while you’re warm inside" from heated floors and a wood burning stove with free firewood. Spikes provided for wonderful winter walks.

Cozy and Romantic Granite Lake Cottage Getaway

Welcome to "Corgi Cottage" ~ your private peaceful getaway to pristine Granite Lake. Enjoy sunrise over the lake from the deck and sunset over the backyard barn. In between, spend the day on the lake in your private sandy cove with dock, fishing, hiking or relaxing. Three mile lake road for walking or biking. The area offers many hiking trails and Mt. Monadnock only 30 minutes away. Small convenience store offers basic amenities while Keene’s many shops and restaurants are only 15 minutes away.

Private Apartment with a Mt. view

*We may make special exceptions for a dog. $50.00 fee per night. *The water from our well is excellent Comfortable, private apartment in a Mid-Century Modern house with stunning views of Mt. Monadnock and farm. 1 Bedroom with Queen Bed w/AC sleeps 2. NOTE: $50 fee for each bed after main bed. Fully equipped Kitchenette, Huge bathroom & Living room -Queen Hide-a-bed sleeps 2. NOTE: We have internet TV, but no cable. So please remember to bring your sign in information for Netflix and Amazon.

Elegant Lodging in the Woods ~Privacy & Comfort!

Looking for a relaxing escape? As Superhosts with 6 years of 5-star reviews, we warmly welcome you to our private, smoke free guest suite. Perfect for couples or solo travelers seeking comfort & tranquility. Tucked away in the peaceful countryside near Pat's Peak & Crotched Mountain, our location offers convenient access to scenic lakes, golfing, hiking, skiing and the charm of rural New England. Enjoy the comfort of serene surroundings & experience genuine hospitality. 75 minutes from Boston.

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

Swim, Hike, Fish, Hot Tub at Waterfront Tiny House

Waterfront oasis. Relax in cozy Tiny House fully equipped with wifi, cable tv, private bath & shower tucked in wooded setting overlooking small waterfall in nature's paradise on Powder Mill Pond and Contoocook River. Hike, Swim, Fish, Kayak, Canoe, Paddle boat. Private fire pit. Hot tub. Eclectic dining, 4 golf courses, shops, breweries, skiing all nearby. Just outside of Peterborough in Southern New Hampshire, only 1.5 hrs from Boston or 2.25 hrs. from Hartford in legendary Monadnock Region.

Cottage beside a waterfall

Our 1840’s renovated grist mill is located in the beautiful Monadnock Region. The house and cottage are situated on twelve acres and includes gardens, an orchard, berry bushes, grape vines, beehives, a dog, and a tremendous waterfall. We are close to many of nature’s gems including Mount Monadnock, Pack Monadnock, the Heald Tract hiking trails, skiing, snowshoeing and swimming. Also the acclaimed MacDowell Arts Center, Andy’s Summer Playhouse, Andres Institute of Art and the Waldorf Schools.

Peaceful Lakefront Escape With a Porch and Kayaks!

Relax on the tranquil shores of Lake Whittemore! Our charming cabin invites you to spend your afternoons paddling with our complimentary kayaks, canoes, and rowboats. After exploring nearby trails, breweries, or ski slopes, enjoy dinner on the screened-in porch, or unwind by the outdoor fireplace. Accommodates six guests with two queen beds and a pull-out couch. Located minutes from the vibrant shops and restaurants of charming Peterborough, this is the perfect nature retreat for any season.

Willow Falls Home ~Hot tub & Waterfront

Constructed waterfall views are just feet away from you! Not far from Boston, RI or CT, this newly designed home is located at a privately viewed pond, in New England, near Mt. Monadnock! Kick back, relax & listen to the water falling in a screened-in gazebo, or in the outdoor hot tub! Or view it all at the picture windows and enjoy the solitude at this picturesque retreat! Inside you'll find multiple lounging areas, luxurious beds, a fully stocked kitchen and a fun game room.

Milling about in history!

Stay for a few nights in the historic Goodell Handle Shop. Relax in the comfort and unique character of this 1851 brick mill building originally part of the Goodell Mills. Two large bedrooms and a cozy room with pullout couch provide you with welcome rest after a day spent in the beautiful Monadnock region. Freshly renovated, the space offers an excellent location walkable to many of Antrim’s quaint amenities like Edmund’s Hardware, Tuttle Library, and Rick and Diane’s restaurant.

HotTub FirePit Games Huge Backyard Family Friendly

The ultimate experience for couples & families 5-10min from hiking trails & ski resorts A Mile from Gregg Lake Beach ALL YEAR PRIVATE/SECLUDED HOT TUB Grill, Hammock, Gym equipment XBox Series S, Life Size Janga, Yahtzee, Darts, Corn Hole, ping pong table, mini pool table Luxury KING PURPLE Brand Mattresses in every bedroom for the best nights rest with individual mini splits for optimal comfort Fully stocked kitchen High speed WiFi, house on 2 private acres

Charming House on 7 Acres in Rural New Hampshire

This magical place has been our home away from home for twenty years and we are excited to share it with you. We hope you'll experience the same time-out-of-time feeling we get when sitting out on the deck in the early morning or looking up on a moonless night as the Milky Way snakes its way across the dark sky. The house sits on seven mostly wooded acres that abut a scenic beaver pond. The property is located on a quiet unpaved road in rural New Hampshire.