Family-friendly vacation rentals in Wakefield

4.99 out of 5 average rating, 118 reviews

The open-concept living area features a sleek gray sofa with decorative pillows and a spacious wooden dining table. Natural light floods the room through large windows, while a wall-mounted TV enhances the entertainment options. The warm wooden ceiling adds a cozy touch.

Cottage in Wakefield

Gorgeous Romantic Lakefront Getaway

Beautiful, 170 feet of waterfront Carriage House with a lovely sandy beach for a relaxing vacation in the Lakes Region of New Hampshire. Very close to the White Mountain National Forest, Kancamagus Highway, and several Ski Resorts. Within 45 minutes to the beaches of Maine and the Seacoast of New Hampshire. Our Carriage House is 1.5 hours from Boston and 2 hours from Worcester, MA. The Carriage House was built in 2021 with top-line finishes, fixtures, and furnishings for a romantic getaway.

Indoor spacesKitchenTV

4.91 out of 5 average rating, 601 reviews

A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.

Treehouse in Sanford

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Indoor spacesFamilySleep quality

4.99 out of 5 average rating, 184 reviews

A modern two-story home is set amidst a wooded area, featuring a spacious outdoor seating arrangement with a picnic table and various chairs. A fire pit and grill are present, with the soft glow of twilight highlighting the inviting exterior.

Cottage in Acton

Eclectic Lakefront Cottage on Great East Lake

Welcome to a relaxing stay on the shores of Great East Lake! The fall and winter are the definition of peace and quiet. Often you'll be the only folks on the cove! Come back inside after your outdoor adventures and warm your feet on the radiant slate floors .You can also prepare a home cooked meal in the vintage, fully applianced kitchen. This home is the perfect base for all your winter excursions, or enjoy family time inside with plenty of games, puzzles, ping pong, or air hockey! Enjoy!

KitchenIndoor spacesDecor

Place to stay in Shapleigh

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

Stay at our one-room Schoolhouse c1866. Winner of Maine Homes Small Space Design Award 2023 and consistently top 1-5% of Airbnb homes for exceptional hospitality, comfort, cleanliness & quintessential romantic New England vibes. The Schoolhouse is 1 of 3 homes on our family's resort-like retreat, Camp Tall Pines: Featuring tennis/pool/gym/sauna, 1000-feet of frontage along the private 80-acre Shapleigh pond (boat/swim/fish), and nestled amongst a majestic 50-acre forest of tall pine trees.

KitchenIndoor spacesLaundry

5.0 out of 5 average rating, 140 reviews

A modern, dark-finished cabin is shown from the side, featuring large windows and a welcoming front porch. The surrounding area is wooded, with tall trees providing natural shade. A gravel driveway leads up to the cabin, enhancing its approachable charm.

4.79 out of 5 average rating, 112 reviews

Pine River Pond

Directly on Pine River Pond, this 5-mile long, 570 acre lake has crystal clear water. This vacation rental is close to all of the area's most popular activities and ensures a memorable time! Swim in the summer, ice fish in the winter, numerous snowmobile trails or just get away from it all.This 1-bath property offers enough space to comfortably accommodate up to 10 guests, making it ideal for a family or group of close friends looking for an unforgettable New Hampshire lakeside retreat.

FamilyKitchenOutdoor spaces

4.98 out of 5 average rating, 124 reviews

The studio apartment features a queen size bed with a striped duvet and two large leather chairs. A wooden desk is positioned near a window, while the warm wooden floor adds to the inviting feel of the space.

Apartment in Wakefield

Clean, quaint studio apartment on small farm

Enjoy the Old Farm cottage, a studio apartment on our small homestead in the beautiful Lakes Region. It’s a perfect spot for couples, small families, or traveling nurses. We are within 20 minutes to many beaches, including Lake Winnipesaukee, and provide easy access to head south to the ocean or north to the mountains. You will have your own separate parking/entrance, but are welcome to enjoy our cozy fire pit, stylish treehouse, and backyard access to the network of snowmobile trails.

Indoor spacesFamilyAccuracy

4.99 out of 5 average rating, 111 reviews

A white horse stands calmly behind a white wooden fence, with verdant green grass surrounding it. The background consists of lush trees, contributing to a serene rural landscape. Soft sunlight illuminates the scene, highlighting the horse's graceful form.

Guesthouse in Wakefield

Peaceful Summertime Retreat: Private Horse Farm

Gorgeous foliage views from the big bay window. A nice 1 mile walking trail. A full kitchen to make homemade meals. A large TV to settle in and relax. A workspace if needed. Laundry. Extra space could be used for storage/air mattress/kid space. Come experience farm life and let us know if you want a visit with any of the animals. Horses, chickens & dogs. Our place is a perfect getaway for a couple or small family. Escape the busy city noise. Relax at our firepit and check out the stars

KitchenFamilyComfort

4.99 out of 5 average rating, 192 reviews

Treehouse in Pownal

The Copper Fox Treehouse

Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen Airbnb's Most wishlisted property in Maine in 2025! Come experience the whimsy and craftsmanship of this red fox head shaped treehouse for yourself. The magic of this wild adventure awaits you in the treetops... Come to relax, explore and make lasting memories your family and friends will talk about for years. Follow our journey on IG at @thecopperfoxtreehouse

FamilyKitchenAmenities

A vibrant sunset unfolds across the horizon, showcasing a gradient of orange, pink, and purple hues against a backdrop of silhouette trees and distant hills. Snow covers much of the ground, reflecting the colors of the sky.

4.97 out of 5 average rating, 115 reviews

Cozy Lakes Region Escape. Fire Pit. Patio

Welcome to Buttercup Inn Tucked away in the peaceful lakes region, less than 2 miles from downtown Wakefield, this tastefully upgraded home may just surprise you. Every detail has been designed to make you feel right at home, from cozy furnishings to the brand new coffee bar- your go-to spot for a perfect brew. Whether you're unwinding or exploring the area, this charming retreat's proof that sometimes the best places are the ones you least expect. Message for further info.

FamilyIndoor spacesBackyard

4.97 out of 5 average rating, 111 reviews

Enjoy Fall Foliage at the Lake

Step out of the house and onto to a beautiful deck. From the deck to the water is just 30 feet of sandy beach! Located right on Pine River Pond, this 5-mile, 570 acre lake has crystal clear water. The gently sloping property makes it ideal for multi-generational families. Swim in the summer, ice fish in the winter or just get away from it all in the fabulous peace and quiet of New Hampshire. Note that June - August rentals are a minimum seven night stays Saturday - Saturday.

FamilyIndoor spacesGetting around

A serene view of the calm lake reflects the blue sky and surrounding pine trees, creating a peaceful atmosphere. A wooden dock extends into the water, offering a space for activities and relaxation.

4.98 out of 5 average rating, 210 reviews

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!

Experience ultimate relaxation with over 100 feet of sandy lakeside beach frontage, nestled among serene pine trees. This spacious lake house features: Open concept main floor 3 levels (3100 sq ft) for privacy Family & dog friendly Hot tub, kayaks, beach, game room, firepit & more! Ideal for large families wanting to share a vacation without compromising on privacy. Enjoy year-round activities and create lasting memories. Get 10% OFF for weekly or longer stays!

Indoor spacesKitchenDecor

4.97 out of 5 average rating, 143 reviews

Cottage in Wolfeboro

Cozy Wolfeboro Getaway | Lake, Ski & Fireplace

Welcome to Lake a Dream - your cozy, family-friendly Wolfeboro getaway in EVERY season! Enjoy our neighborhood beach just a 5-minute walk away or explore charming downtown Wolfeboro, only 5 minutes from the cottage. Winter is just as magical! Ski at Wolfeboro’s hidden gem, Abenaki Ski Area, skate, snowshoe or simply cozy up by the fireplace with hot cocoa & family games. Looking for a bigger mountain day? Gunstock & King Pine are nearby too!

FamilyKitchenGetting around

Popular amenities for Wakefield family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 272 reviews

Cabin in Barnstead

Dreamy Lakefront: Hot Tub, Kayaks, & Kid-friendly

KitchenFamilyHeating

4.96 out of 5 average rating, 191 reviews

Home in Shapleigh

Lakehouse/HottubFirePit/2pvtdocks/SUPs/YAKs/LgYard

FamilyIndoor spacesAccuracy

4.97 out of 5 average rating, 244 reviews

The cabin is illuminated warmly at dusk, featuring a hot tub in the backyard. Outdoor seating arrangements with four chairs are positioned around a fire pit, set against a backdrop of trees, creating a serene and inviting atmosphere.

Cabin in Kennebunk

HotTub/5min to K-port, Pet friendly, @anchorunwind

KitchenIndoor spacesLocation

4.97 out of 5 average rating, 197 reviews

Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

Indoor spacesKitchenSolo travel

4.98 out of 5 average rating, 173 reviews

Home in Saco

Oceanfront Escape • Walk to Beach • Sleeps 14

KitchenFamilyLayout

Superhost

The two-story lakeside house features large windows and a spacious deck with seating. A private dock is visible in front, with lounge chairs arranged on the sandy beach nearby. Lush greenery surrounds the property, creating a serene outdoor space.

Home in Middleton

Blue Breeze - Private lakefront w/ Hot Tub

FamilyIndoor spacesDecor

4.88 out of 5 average rating, 226 reviews

4.9 out of 5 average rating, 120 reviews

Cabin in Sanford

Campfires & Porch Swings Jacuzzi + Pets welcome

FamilyIndoor spacesWalkability

5.0 out of 5 average rating, 103 reviews

Cabin in Norway

Secluded Cabin: Mountain View, Hot Tub + Fireplace

Indoor spacesFamilyHospitality

Family- and pet-friendly home rentals

4.9 out of 5 average rating, 101 reviews

A spacious living area features a large sectional couch with built-in cupholders, facing a wall-mounted TV. A wooden coffee table sits in the center, surrounded by a decorative plant and various board games. Natural light enters through nearby windows, enhancing the warm ambiance.

Chalet in New Durham

Mountainside Chalet w/Sauna near Gunstock Resort!

KitchenFamilyCleanliness

4.92 out of 5 average rating, 126 reviews

A retro camper is situated on a wooden deck, framed by potted plants. Bright orange chairs are placed at a small table underneath a striped awning, providing shade. Decorative bunting hangs along the side, with a backdrop of lush, green woods.

Camper/RV in Milton

Retro Camper on farm property in Lakes Region, NH

FamilyKitchenAccuracy

4.96 out of 5 average rating, 261 reviews

A relaxing outdoor area is shown, featuring several seating options around a fire pit. Two cabins can be seen, with one situated on a hill and the other by the water. A sun umbrella provides shade, surrounded by trees and nature.

Chalet in Standish

Blueberry Hill

Indoor spacesKitchenValue

Cottage in Moultonborough

A well-maintained lawn leads to a serene lake view, with a flagpole displaying an American flag. A covered boat dock and several trees line the water's edge, while a pet can be seen on the grass, contributing to the tranquil atmosphere.

The Lake house

KitchenIndoor spacesCleanliness

4.96 out of 5 average rating, 116 reviews

4.96 out of 5 average rating, 102 reviews

A rustic white barn with a grey roof is nestled within a field of tall grasses and wildflowers. Autumn foliage in shades of red and gold decorates the surrounding trees, offering a tranquil rural landscape. A separate red cottage is visible in close proximity.

Guesthouse in Denmark

Red Shed Cottage at Pickett Hill Farm

Indoor spacesKitchenAccuracy

5.0 out of 5 average rating, 12 reviews

Bear Point - 4 Bedroom home on the water

Indoor spacesFamilyCondition

4.94 out of 5 average rating, 17 reviews

Renovated Luxury Lakefront w/ Beach/Dock/firepit

KitchenFamilyGetting around

4.93 out of 5 average rating, 46 reviews

In the Trees - NH w/ Lake Access

Indoor spacesFamilyOutdoor spaces

Family-friendly home rentals with a pool

4.91 out of 5 average rating, 286 reviews

An aerial view captures a serene lakeside setting, featuring a sandy beach lined with lounge chairs. Several boats are docked along the shore, while trees and buildings provide a natural backdrop, creating an inviting space for outdoor relaxation and activities.

Condo in Gilford

Great Condo near Gunstock, Lake Access & Concerts

Indoor spacesFamilyAir conditioning

4.9 out of 5 average rating, 117 reviews

Condo in Wells

Starfish Condo Wells Beach

FamilyIndoor spacesLaundry

5.0 out of 5 average rating, 103 reviews

A heated pool is set within a stone patio, surrounded by lush greenery. Two lounge chairs are positioned nearby, while modern heating units stand along the patio's edge. The pool's clear water reflects the surrounding area, offering a serene outdoor retreat.

Home in Ogunquit

Ogunquit Village 5 BDR, Heated Pool, Walk to Beach

Indoor spacesFamilyBackyard

Home in Old Orchard Beach

OOB Oasis: 6BR Home w/ Private Pool Near Beach

KitchenFamilyHot tub

4.95 out of 5 average rating, 155 reviews

5.0 out of 5 average rating, 100 reviews

An aerial view of the property displays a spacious yard with a well-maintained in-ground saltwater pool surrounded by wooden decking. A barrel sauna and fire pit are positioned nearby, complemented by manicured greenery and tall coniferous trees in the background.

Home in Meredith

1840 Meredith Farmhouse w/ outdoor Sauna & Pool

FamilyKitchenPool

5.0 out of 5 average rating, 146 reviews

Townhouse in Lincoln

Loon Views · 3BR King + Bunkroom

KitchenFamilyBathroom

4.97 out of 5 average rating, 174 reviews

A welcoming living area is furnished with two dark sofas adorned with vibrant orange cushions. A rustic coffee table is centered on a colorful area rug, while large windows allow natural light to fill the space, highlighting the wall art above.

Home in Portland

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

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