Vacation rentals in Bennington

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.

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.

Modern Quiet Lakeside Retreat

Come relax at our newly renovated lakefront home on Gregg Lake! Our spacious and modern home is located on a quiet cove of this 200 acre lake that boasts a variety of fun water activities. Enjoy the use of our kayaks, paddle boards and peddle boat or try your luck at catching some local bass with our fishing rods! You will also love the scenic sunsets you can view from our large deck that overlooks the lake. Tons of amenities included so that we can make your stay comfortable and stress free.

Midcentury retreat at Zulip Farm

This beautiful house is the ultimate city escape located just 90 minutes from Boston! The unique and spacious design opens up to the outside, letting you enjoy the great outdoors through a wall of windows from a cozy sunken living room. In the summer, lounge by the pool or enjoy one of two pristine lakes 10 minutes away. In winter, only 15 minutes to Pat’s Peak and 20 minutes to Crotched Ski Resort. Please review the waiver language below, which we will require you to sign after booking.

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.

Direct Waterfront A-Frame, Close to 3 Ski Areas!

My direct waterfront, year-round A-Frame cabin is 30 min to Mount Sunapee, 20 min to Crotched, and 15 min to Pat's Peak! It’s located on a small 32-acre pond near Franklin Pierce Lake with over 100 feet of waterfront. There is a 6 foot main dock to load kayaks, and a small fishing dock off to the side. The fishing on our pond gets rave reviews! The property sits on 1/3 of an acre, on a sloped hill. It's located between Keene and Concord, and nearby many great hiking and snowmobile trails

Quiet House in the Woods

Relax with the whole family at this peaceful place to stay. - Gregg Lake 5 mins away (Swim, Volleyball, Swings, Boat Docks) - Great hiking trails (Monadnock & Miller State Park) - Ski in the winter (Crotched Mountain 20 mins away, Pats Peak 30 mins away) - Small town: Mom & Pop shops/restaurants, Antique stores - 2 Decks: Out door dining & sitting areas This is not an investment property, this is my home. Please be respectful of the property. Thank you! Hope you enjoy your stay!

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.

The Harrisville Ranch - Monadnock Region Getaway!

Located in the heart of the Monadnock Region and surrounded by forests and lakes the Harrisville Ranch is ready to host you! With 4 bedrooms it is great for groups & families visiting the area for hiking, weddings, or just a getaway to a quaint NH village. Mount Monadnock: 5-15 minutes depending on the hiking trail Dublin School: 5 minutes Aldworth Manor & Mayfield Farm Venues: 8 minutes Harrisville Center: 5 minutes Peterborough: 15 minutes Hancock: 15 minutes Keene: 20 minutes

Wood-Fired Sauna & Cold Plunge Farmhouse

“Retreat to our 3BR/3BA home on 7 acres of historic farm land in Deering, NH. Sleeps 7 with game room, family room and 3-season porch overlooking fields & conservation land. Gather by the patio for BBQ and outdoor dining or relax in the 6-person wood fired sauna with cold plunge. Just 40 min from Manchester Airport, close to ski slopes, lakes, and trails—perfect for both adventure and renewal. *additional amenities include dart board, small massage chair & ping pong”

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.