Family-friendly vacation rentals in Milton

4.97 out of 5 average rating, 212 reviews

A weathered sign reading 'Rose Cottage' hangs from a tree, with vibrant autumn leaves surrounding the area. A quiet road is visible in the background, framed by trees, creating a serene and inviting atmosphere.

Guest suite in Lebanon

Rustic Rose Cottage of Historic West Lebanon

Rustic guest suite on serene four acres. Abutting colonial cape style house and West Lebanon Historic District date back to early 18th Century. Private parking & entrance, queen memory foam mattress, steam sauna, kitchen and laundry supplies, and desk and high speed wifi for telework. Minutes from Skydive New England, Prospect Hill Winery or McDougal Orchard. 30min to Portsmouth NH, Maine beaches, and Lake Winnipesaukee. Just over an hour to the White Mountains, Portland ME or the Boston area.

FamilyIndoor spacesOutdoor spaces

4.95 out of 5 average rating, 144 reviews

An A-frame cabin showcases a wooden exterior with large glass windows, allowing natural light indoors. The deck features four Adirondack chairs arranged around a circular fire pit. Surrounding greenery and autumnal trees enhance the serene outdoor setting.

Cabin in Danbury

Cozy A Frame Cabin

Discover Your Dream Getaway at Our Enchanting A-Frame Cabin in Danbury, NH! Hike lush forest trails, paddle across sparkling lakes, or hit the nearby slopes for seasonal adventure. After a day outdoors, kick back on the spacious deck, fire up the grill, and dine under the stars. Whether you're planning a romantic escape or a fun-filled family getaway, this hidden gem offers the perfect blend of comfort, charm, and natural beauty. Escape the ordinary—book your unforgettable Danbury retreat today!

Indoor spacesKitchenAccuracy

4.91 out of 5 average rating, 593 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.

KitchenIndoor spacesCheckout

4.9 out of 5 average rating, 579 reviews

A serene outdoor space features a fire pit surrounded by natural stone. Lush greenery extends to distant mountain views under a partly cloudy sky, creating a peaceful setting for relaxation and outdoor gatherings.

Cabin in Tamworth

Secluded Mountain View Cabin • Private Sauna

A real cabin in the North Woods secluded, private, and surrounded by open sky and sweeping mountain views that remind you why you came. This log-style retreat sits deep in the woods above Tamworth, fully equipped for comfort without sacrificing the rugged feel. Hike local trails, stargaze in near-zero light pollution, or sit by the fire pit with the mountains in front of you. The optional wood-fired sauna steps from the door is the perfect end to the day. Sauna available as a one-time add-on.

FamilyIndoor spacesWifi

4.89 out of 5 average rating, 221 reviews

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

This huge lakeside house is a great experience for all of your friends and family to enjoy all the New Hampshire lakes region has to offer. There is incredible nature all around! Some of our favorites nearby: 11min to a nearby brewery 12min to a great breakfast spot 14min to a farm stand and pick-your-own produce 17min to a nearby winery 21min to Hannafords grocery store 22min to Alton Bay 25min to Wolfeboro 29min to Mt. Major with views of Winnipesaukee 38min to Gunstock mountain for skiing

FamilyKitchenCheckout

Place to stay in Shapleigh

5 out of 5 average rating, 133 reviews

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.

FamilyIndoor spacesAccess

4.98 out of 5 average rating, 318 reviews

Cabin in Alexandria

Mountain Lodge with Private Sauna

Escape to Darkfrost Mountain Lodge, less than 2 hours from Boston - Gather under the stars by the fire pit & garden - Relax or grill on patio with woodland views - Enjoy a pet-friendly working homestead - Ski at nearby Ragged & Tenney Mountain - Explore hiking, biking & snowshoeing nearby at Wellington, Cardigan Mountain State Parks, AMC Cardigan Lodge Looking for options? Visit my Airbnb Host Profile to explore our 3 available cabins: Millmoon A-Frame, Black Dog Cabin, Darkfrost Lodge.

FamilyIndoor spacesParks

4.95 out of 5 average rating, 354 reviews

The living area features a blend of comfortable seating, including a dark brown recliner and a soft sofa. A wooden coffee table is centrally placed, adorned with decorative items. Natural light illuminates the space, complemented by neutral walls and subtle décor.

Home in Lebanon

Tranquility, Relaxation, Family, Romance

Bring your family or have a romantic getaway in this beautiful 2 bedroom, 2 private baths located in this quiet country setting. Pet friendly. Big fenced in wooded back yard for your pets to roam. Big back yard deck w/ seating, grill. Minutes away to boat launching area to rent party boats, kayaks, paddle boats, Swimming, winter sports on Milton 3 ponds. Seasonal blueberry, peach, apple picking in town. Park your boat or snowmobile trailors. Skydive New England right in town. Fall leaves.

Indoor spacesFamilyNearby

4.93 out of 5 average rating, 1,133 reviews

A winding wooden boardwalk, framed by trees, leads to a treetop sanctuary. The path is bordered by a vibrant orange railing, contrasting with the natural greenery. The treehouse structure is nestled above, showcasing a charming entryway and seasonal decorations.

Treehouse in Dunbarton

Treetop Sanctuary

Get away from life at the treetop sanctuary! Follow the suspended path through the trees to your own little treetop oasis. This standalone space rests 30 feet above the forest floor. The space is perfect for reconnecting with nature. Amenities: Elec. WIFI, Compost toilet, Woodstove (I supply firewood), Fridge. Bring; *SLEEPING BAGS* or Blankets/Linens (queen size) Pots and pans, (If You wish to cook on the stove) Accepting children 10 +up. Absolutely no pets. 4wd/awd during winter pls.

FamilyIndoor spacesAmenities

4.98 out of 5 average rating, 115 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.

KitchenIndoor spacesGetting around

4.97 out of 5 average rating, 175 reviews

A cozy cottage exterior is shown, featuring light-colored siding and a welcoming wooden entrance deck. Surrounding greenery enhances the tranquil setting, while a driveway leads to the property. The serene lake is visible in the background, surrounded by trees, inviting a peaceful retreat.

Cottage in Middleton

Beautiful Lakeside Cottage

Beautiful, quiet and secluded lakeside cottage. Enjoy amazing sunsets on our pristine lake. Swim, kayak, fish or just relax and take in the natural beauty. COVID UPDATE: We know everyone has different levels of concern regarding the virus. Please know that while we feel our sanitation and cleanliness of the Cottage is exceptional, we have doubled our efforts providing multiple cleanings between guests. This is a NON-SMOKING property. We are sorry, but we cannot accommodate pets.

Indoor spacesKitchenAccuracy

4.97 out of 5 average rating, 231 reviews

A serene lakeside view is presented, featuring a well-maintained garden with colorful flowers and lush greenery. Smooth stones create a path leading towards the calm waters of Sunrise Lake. The dock and surrounding trees are visible under a bright blue sky with scattered clouds.

Cottage in Middleton

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks

Escape to a peaceful, lakeside retreat with a secluded sun-lit deck and private dock with incredible views of Sunrise Lake, plus a 4-person hot tub, and seasonal amenities like a pedal boat, two kayaks, a SUP board, gas fire table, central A/C, a pellet stove, and snowshoes. Enjoy nearby activities like hiking, leaf peeping, skiing, and visiting scenic towns, local vineyards and breweries — or simply relaxing in a beautiful lakefront setting. The sunsets can be unbelievable!

Indoor spacesKitchenGetting around

Popular amenities for Milton family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 160 reviews

An expansive view of rolling mountains is captured in the distance, flanked by vibrant trees displaying a palette of greens and hints of autumn colors. The landscape is rich with varying elevations, inviting exploration of the natural beauty surrounding the property.

Camper/RV in Benton

Private White Mountain RV Camping - VIEWS+HOT TUB!

Indoor spacesFamilyAmenities

4.94 out of 5 average rating, 111 reviews

Home in Conway

Luxe Lodge in the Woods! With Sauna & Hot tub

KitchenFamilyHiking

4.96 out of 5 average rating, 393 reviews

Home in Acton

The LOTUS welcomes you, stay a while

FamilyKitchenHot tub

5 out of 5 average rating, 309 reviews

A modern cabin with an A-frame shape is illuminated by warm lights, surrounded by tall trees. In front, a fire pit with wooden chairs invites gatherings, while a hot tub and sauna are visible nearby, contributing to the outdoor relaxation space.

Cabin in South Berwick

Romantic A-Frame cabin in the woods

KitchenIndoor spacesCheck-in

4.98 out of 5 average rating, 191 reviews

The cabin exterior is showcased with large glass walls, allowing natural light to fill the interior. A wooden deck is lined with outdoor lights, leading to a hot tub. Surrounded by trees, the peaceful setting is visible, creating a serene outdoor atmosphere.

Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

KitchenFamilyCheck-in

4.95 out of 5 average rating, 270 reviews

Cabin in Barnstead

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

KitchenFamilyGetting around

4.99 out of 5 average rating, 182 reviews

The living area features a high, wooden ceiling with large windows that provide natural light and views of the surroundings. A stone fireplace is positioned centrally, flanked by comfortable seating. A dining area and modern kitchen appliances are visible in the background.

Home in Hebron

Luxurious Eagle Ridge Log Home at Newfound Lake

Indoor spacesKitchenHeating

4.94 out of 5 average rating, 242 reviews

A spacious stone courtyard features a large stone fireplace surrounded by seating areas. Potted plants add greenery to the space, with outdoor furniture, including a table and chairs, positioned for relaxation. Strings of lights outline the patio, creating a welcoming ambiance.

Cabin in Rochester

awesome private cabin

Indoor spacesFamilyNearby

Family- and pet-friendly home rentals

4.99 out of 5 average rating, 143 reviews

A single-story cottage is nestled among trees, featuring a light yellow exterior with dark shutters. The well-kept front yard showcases a carpet of fallen leaves, and a small deck is visible to the right, enhancing access to the inviting outdoor space.

Cottage in Alton

“Stay Awhile in the Lake's Region”

Indoor spacesFamilyDecor

5 out of 5 average rating, 30 reviews

The cottage exterior is framed by lush greenery and vibrant flowers in planters. The charming blue siding contrasts with the surrounding pines and sunlight dappling through the trees. A clear pathway leads to the entrance, enhanced by a stone border along the flower bed.

Cabin in Milton

Cozy cottage near the lake

Indoor spacesKitchenCheckout

4.98 out of 5 average rating, 150 reviews

An open floor plan is showcased, featuring a cozy futon couch with decorative pillows. A wooden staircase leads to the loft, while large windows allow natural light to illuminate the space. Basic kitchen supplies are visible on the wooden countertop.

Cabin in Standish

THE LILLIPAD.Off-grid A frame. Sebago lake region!

Indoor spacesKitchenRiver

4.96 out of 5 average rating, 141 reviews

Home in Epsom

Epsom Lakefrnt Escape~Dock~Grill~Firepit-Woodstove

Indoor spacesKitchenBiking

4.85 out of 5 average rating, 952 reviews

Tiny home in Epsom

1 Bed Cabin - Postcard Cabins, Blake Brook

FamilyIndoor spacesAccess

4.93 out of 5 average rating, 201 reviews

A modern cabin sits amidst lush greenery, with large windows reflecting soft evening light. A serene creek runs nearby, while a cozy fire pit and chairs are positioned outside, inviting relaxation in nature.

Cabin in Woodstock

Cabin HYGGE at Lumen Nature Retreat | Elin

KitchenFamilyOutdoor spaces

4.88 out of 5 average rating, 184 reviews

A charming log cabin is set amid lush greenery, featuring a stone chimney and a welcoming front porch. The rustic wood exterior seamlessly blends with the surrounding trees, creating an inviting atmosphere. A gravel pathway leads to the entrance, accented by blooming plants.

Home in New Durham

Inviting cabin getaway

Indoor spacesKitchenLayout

Place to stay in Moultonborough

A rustic wooden cabin is nestled among snow-covered trees, with a clear path leading to its entrance. An American flag is displayed by the window, and fallen leaves around the cabin contrast against the fresh snow.

4.98 out of 5 average rating, 165 reviews

The Bear's Den: 40 acre Off-Grid Retreat +Gator

Indoor spacesFamilyGetting around

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 248 reviews

A small red cabin with a green metal roof is surrounded by trees and rocks. Flower boxes are mounted under the windows, adding a touch of color. A patio area is visible nearby, featuring chairs and an umbrella for shade.

Tiny home in Thornton

Basecamp in the White mountains

Indoor spacesFamilyOutdoor spaces

4.88 out of 5 average rating, 312 reviews

A spacious room features a large bed with plush bedding against a warm-toned wall. A relaxing jetted tub is positioned beside it, with soft lighting provided by bedside lamps. A window allows natural light to enter, enhancing the overall calm and comfortable ambiance.

Apartment in Bartlett

Attitash Retreat

Indoor spacesKitchenCleanliness

4.87 out of 5 average rating, 174 reviews

A gentle river flows over smooth, rocky surfaces, creating soft white rapids. Surrounding the water, a mix of evergreen and deciduous trees line the banks. A clear blue sky is visible above, enhancing the natural landscape.

Condo in Bartlett

Spacious Condo-Attitash Ski-Storyland-Saco & More!

Indoor spacesKitchenComfort

4.93 out of 5 average rating, 265 reviews

A spacious living room features a large sectional couch and an accent chair, both positioned on a patterned area rug. A wall-mounted TV is visible, with light streaming through the windows, highlighting the natural wood flooring and airy design.

Home in Derry

Sanctum by the Lake

FamilyIndoor spacesHospitality

4.91 out of 5 average rating, 109 reviews

Condo in Wells

Starfish Condo Wells Beach

KitchenFamilyQuiet

4.96 out of 5 average rating, 122 reviews

A modern kitchen is showcased with white cabinetry and granite countertops. Stainless steel appliances include a refrigerator, microwave, and dishwasher. Kitchenware is neatly arranged, enhancing the functional space. A light blue wall adds a calm touch, while a throw pillow with 'BEACH.' text provides a decorative element.

Condo in Wells

Steps to Wells Beach + Pool | Coastal Retreat

Indoor spacesFamilyComfort

4.92 out of 5 average rating, 118 reviews

A welcoming living area features warm wood flooring and natural light from multiple windows. Comfortable seating includes a sofa and chairs arranged around a central table. A ceiling fan provides gentle airflow, while double French doors lead to an outdoor space.

Guest suite in Standish

Steep Falls Escape, river & falls just steps away

KitchenFamilyHospitality