Holiday rentals in Chatham

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Top-rated holiday rentals in Chatham

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Top guest favourite
The exterior of the chalet showcases a striking design with a sloped roof and large windows. Soft lighting emanates from within, creating a warm glow against the dark wood finish. Surrounding greenery enhances the natural setting, while a deck with a patio umbrella is visible.
Cabin in Stoneham
4.99 out of 5 average rating, 208 reviews

Mad Moose Lodge• Secluded Cabin w/ Mountain View’s

Welcome to the Mad Moose Lodge! Year-round adventures begin at this 2-bed, 2.5-bath Stoneham chalet. This vacation rental provides incredible fall foliage views and easy access to mountains and lakes! Close by to cross-country skiing and snowshoeing in the winter and hiking, mountain biking, boating and swimming in the summer there are endless options of outdoor enjoyment. Enjoy stunning sunsets over the mountains from the comfort of the couch, or while enjoying a game of pool in the game room!

Top guest favourite
A large window offers a view of rolling mountains adorned with colorful autumn foliage. Shades of red, orange, and yellow contrast against the green trees, while a winding path is visible in the foreground, leading into the vibrant landscape.
Guest suite in Conway
4.98 out of 5 average rating, 632 reviews

Mountain View Studio

This over-garage studio has a private entrance, a queen-sized bed, a futon, gas fireplace, kitchenette & bathroom. There is a refrigerator/freezer, microwave, coffeemaker & toaster but no oven/stovetop. There is a small gas grill available May-Oct. We have beautiful mountain views & are located 10 minutes from downtown. NOTE: Our driveway is long and steep. 4WD/AWD vehicles are often needed to safely get up our driveway in the winter. Also, you will hear the garage door when it opens & closes.

Guest favourite
A well-lit chalet is visible in the background, showcasing its large windows. In the foreground, a stone fire pit surrounded by five adirondack chairs is highlighted, with glowing embers and flames creating a warm ambiance against the night sky.
Cabin in Fryeburg
4.94 out of 5 average rating, 287 reviews

Cozy Cabin*Hot Tub*Lake Access w/Beach*A/C*Dogs OK

The LV Chalet is located less than 30min to popular North Conway, N.H./15 min to Historic Fryeburg, Maine. The Chalet is ideal for couples, friends & families to relax! In the Summer, enjoy beach access to Lower Kimball Lake, nearby Saco River and year round hiking trails. In the winter, the Chalet is situated between ski mountains: Cranmore Mountain & Pleasant Mountain. There’s also close access to Snowmobile trails. Whatever your vacation interests are; the area boasts it all! No partying pls

Guest favourite
A private hot tub is surrounded by trees displaying vibrant autumn leaves, with a gentle stream flowing nearby. A fire pit sits beside the hot tub, offering a cozy gathering space. The cabin's exterior features wooden siding and large windows that invite natural light.
Tiny home in Norway
4.93 out of 5 average rating, 246 reviews

Glass Wall Waterfront Hot Tub Fireplace Tiny Home

Wake up to rushing waterfalls right outside your glass wall in this romantic waterfront tiny home in Norway, Maine! Private hot tub with river views, see-through gas fireplace, cozy raised queen bed overlooking the water, outdoor shower, hammocks, and direct access to hiking trails. Total privacy—no neighbors in sight. Modern kitchen, heated floors, fast WiFi, and thoughtful touches for couples or solo escapes. Romantic getaway near Sunday River skiing, golf & Maine adventures. Nature's oasis

Top guest favourite
A modern kitchen features sleek countertops and high-end appliances, including a stainless steel oven and range. Black pendant lights hang above a spacious island with bar stools. Multiple windows allow for abundant natural light, with a patterned rug adding warmth to the wooden floors.
Guest house in Hiram
5 out of 5 average rating, 131 reviews

1BR cozy, luxurious getaway @ Krista's Guesthouse

Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

Superhost
A rustic yurt is situated within a rich green forest, featuring a wooden deck and steps leading up to its entrance. The yurt is partially covered with a green canvas exterior, and a small white chair is placed on the porch, blending with the natural surroundings.
Yurt in Chatham
4.85 out of 5 average rating, 309 reviews

Cozy Yurt in the Peaceful Woods

Handcrafted and built with locally sourced wood, this yurt offers 300+ sq ft of open, circular space with a high ceiling and soft natural light. It comfortably sleeps up to four with a queen mattress and folding sofa bed. The yurt is fully insulated with woodstove heat to keep things warm on cool mountain nights. Powered by solar energy for lights and phone charging. Enjoy the private fire pit under the stars. A private outhouse is available onsite. Site available year-round.

Guest favourite
A panoramic view encompasses rolling green hills and distant mountains under a partly cloudy sky. Rocky outcroppings frame the foreground, while a series of chairs are positioned invitingly for enjoying the scenery. Lush trees add depth to the natural landscape.
Guest house in Jackson
4.87 out of 5 average rating, 121 reviews

Best View in New Hampshire

"Best View in New Hampshire" Guest House is nestled in the White Mountains and sits nine miles east of Mount Washington. It offers hiking, serenity, and the best panoramic views of the Presidential Range in all of the Mount Washington Valley. So whether you prefer to marvel at sunrises or sunsets, this is the place for you. You are close by to The Town of Jackson, StoryLand, Red Fox Bar & Grille, Yesterday's, Sunrise Shack, and direct access to Tin Mine Hiking Trail.

Top guest favourite
A two-story white farmhouse is set amongst greenery, featuring a blue metal roof and a charming front door. Two stylish chairs with decorative cushions are positioned on the front porch, which is framed by trees and lush grass, offering a welcoming outdoor space.
Guest suite in Fryeburg
4.99 out of 5 average rating, 275 reviews

A little slice of heaven!

Spring has finally sprung! Cmon up for a weekend getaway! Daffodils are popping and the fields are green! Unique guest suite in the midst of wide-open mountain views in farm country. Comfortable airy rooms, full bath & your own living room with games, puzzles, books, cable tv and WiFi. Complimentary coffees, teas and cold drinks. Keurig, microwave and mini fridge at your disposal. Great for couples, families, girls weekends! Come and see what all the buzz is about!

Top guest favourite
The treehouse exterior is softly illuminated by string lights, casting a warm glow among the surrounding trees at dusk. A wooden hot tub is visible on the deck, with a set of steps leading up to the main entrance nestled among boulders.
Treehouse in Woodstock
4.98 out of 5 average rating, 300 reviews

Treehouse With Hot Tub Close to Sunday River!

Escape to an authentic luxury treehouse designed by B’Fer Roth of DIY Network’s Treehouse Guys and built by The Treehouse Guys. Hidden on a private wooded road with no neighbors in sight, this unique retreat borders 626 acres of Bucks Ledge Community Forest with 7 miles of trails right outside your door. Enjoy peaceful seclusion just 15 minutes to Sunday River, 5 minutes to Mt. Abram, and 10 minutes to Bethel for the perfect mix of adventure and relaxation.

Top guest favourite
A lofted bedroom features a spacious bed adorned with a vibrant striped blanket. Light filters through a window, highlighting the sloped whitewashed ceilings and simple artwork on the walls. Warm wood accents complement the soft, neutral tones throughout the room.
Home in Bridgton
4.98 out of 5 average rating, 170 reviews

Wren Cabin + Wood fired Sauna

We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.

Top guest favourite
The spacious interior features wooden beams and warm, rustic tones. A large bed is centrally positioned, accompanied by a wooden chest. A cozy seating area includes a rocking chair and lamps, while a dining table near windows offers natural light and views of the surroundings.
Guest suite in Conway
5 out of 5 average rating, 384 reviews

CloverCroft - "Far from the madding crowd."

CloverCroft, a 200+/- year old farmhouse, is located in the rich farmland of the Saco River Valley at the foot of the White Mountains. We go the extra mile to make your stay enjoyable and comfortable. (Please note our mattress is FIRM and there is a long flight of outdoor stairs to access the suite.) COME ENJOY PRIVACY AND THE GREAT OUTDOORS. There are many summer and winter activities very close by and we look forward to hosting you.

Guest favourite
An aerial view captures a vibrant riverside cabin, surrounded by lush greenery and tall trees. The property sits beside a rocky stream, with a pathway leading up to the cabin's entrance, creating a serene and inviting outdoor setting.
Cabin in Intervale
4.86 out of 5 average rating, 205 reviews

Riverside|Sauna|Hot tub|Pizza Oven|Dogs

Step into riverside magic at this upscale retreat. With a king room, queen room, and kid-friendly bunk nook, this dreamy escape features a wood-fired sauna, hot tub, luxe SMEG appliances, a pizza oven, herb garden, gas fireplace, fire pit, espresso bar, outdoor ping pong, and a spa-like bath with double shower. Dog-friendly and unforgettable—this place isn’t just a stay, it’s a story. Miss it, and you’ll wonder what could’ve been.

Popular amenities for Chatham holiday rentals

  1. Airbnb
  2. United States
  3. New Hampshire
  4. Carroll County
  5. Chatham