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Family-friendly vacation rentals in Milton

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Quick stats about vacation rentals that are family-friendly in Milton

  • Total vacation rentals

    Explore 40 vacation rentals in Milton

  • Nightly prices starting at

    Milton vacation rentals start at G$29,289 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,890 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Milton vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Milton rentals

  • 4.9 Average rating

    Milton stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Milton

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
Home in Shapleigh

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

Bring your family/friends for a fun and relaxing stay on Mousam Lake all year round! With 3 bedrooms, and additional loft and a basement sleeping area, there's room for everyone! Explore the lake with canoes, kayaks and paddleboards available to you or bring your own boat, the public boat launch is across from our front dock! When you are not enjoying the lake, the house provides many spaces for your favorite yard games, a screen house to play cards or have a drink and unwind in large hot tub!

FamilyIndoor spacesPets

4.96 out of 5 average rating, 191 reviews
Top guest favorite
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.

KitchenFamilyBackyard

4.91 out of 5 average rating, 601 reviews
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

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

Indoor spacesFamilyAmenities

4.88 out of 5 average rating, 226 reviews
Top guest favorite
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 spacesQuiet

4.99 out of 5 average rating, 184 reviews
Top guest favorite
Cabin in Barnstead

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

This romantic & family-friendly lakefront chalet comes with a private beach, hot tub, kayaks & stunning views and is packed with amenities. It’s a serene home base to explore some of the best New England towns and is in the heart of the Lakes Region. Swim, kayak, bike a scenic trail, fish, hike, explore historic towns, farms & food scene, or simply grill with a view & play board games. We have poured our heart into making this a romantic yet very kid-friendly retreat (kids gear included).

Indoor spacesKitchenView

4.95 out of 5 average rating, 272 reviews
Top guest favorite
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.

FamilyKitchenDecor

4.95 out of 5 average rating, 376 reviews
Top guest favorite
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 spacesLaundry

4.98 out of 5 average rating, 124 reviews
Top guest favorite
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 spacesFamilyOutdoor spaces

4.97 out of 5 average rating, 181 reviews
Top guest favorite
Home in Wakefield

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.

KitchenIndoor spacesOutdoor spaces

4.97 out of 5 average rating, 111 reviews
Top guest favorite
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!

KitchenIndoor spacesGrill

4.97 out of 5 average rating, 236 reviews
Top guest favorite
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

Come experience this beautifully restored 1969 retro camper in a rural wooded setting. Located in the lakes region, it is close to hiking, swimming, apple orchards, as well as popular restaurants. Only 1 hr from Portland and 1.5 hrs from Boston. The camper is on a private and quiet 7-acre farm. The camper has a toilet, very small shower, sink, cooktop, fridge, and small microwave. The camper is very small w a tiny bathroom but cozy and comfortable. LGBTQ+ friendly.

FamilyIndoor spacesBeach

4.92 out of 5 average rating, 126 reviews
Top guest favorite
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!

FamilyIndoor spacesBathroom

4.97 out of 5 average rating, 143 reviews

Popular amenities for Milton family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
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.
Home in Wakefield

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

KitchenFamilyBackyard

4.98 out of 5 average rating, 210 reviews
Guest favorite
Cabin in Sanford

Campfires & Porch Swings Jacuzzi + Pets welcome

KitchenIndoor spacesLocation

4.9 out of 5 average rating, 120 reviews
Top guest favorite
Guesthouse in Alton

Vineyard Terrace - Modern & Beautiful

KitchenFamilyHospitality

4.98 out of 5 average rating, 335 reviews
Top guest favorite
Place to stay in Shapleigh

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

KitchenIndoor spacesLayout

5.0 out of 5 average rating, 139 reviews
Top guest favorite
Home in Saco

Oceanfront Escape • Walk to Beach • Sleeps 14

KitchenFamilyAmenities

4.98 out of 5 average rating, 173 reviews
Top guest favorite
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 spacesCleanliness

4.97 out of 5 average rating, 244 reviews
Top guest favorite
A contemporary cabin retreat is nestled among tall trees, softly illuminated by warm outdoor lights. A wooden deck with steps leads to a welcoming entrance. A separate sauna structure is visible, surrounded by snow-covered ground, providing a serene atmosphere in a tranquil forest setting.
Home in South Berwick

Romantic Mirror cabin in the woods

Indoor spacesLocationAccuracy

5.0 out of 5 average rating, 146 reviews
Top guest favorite
An aerial view of the equine estate showcases a blend of green fields and autumn foliage. The main building, featuring a dark roof, is bordered by trees and leads to a well-maintained driveway. Nearby, two red barns complement the rural landscape.
Farm stay in Loudon

Unique Equine Estate w/an Indoor Pool & Hot Tub.

KitchenIndoor spacesParks

4.95 out of 5 average rating, 108 reviews

Family- and pet-friendly home rentals

Superhost
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

FamilyIndoor spacesBackyard

4.87 out of 5 average rating, 188 reviews
Top guest favorite
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

FamilyKitchenGrill

4.96 out of 5 average rating, 261 reviews
Top guest favorite
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!

Indoor spacesKitchenCondition

4.9 out of 5 average rating, 101 reviews
Top guest favorite
An aerial view displays a colonial home surrounded by vibrant autumn foliage, set on an expansive lawn. The nearby Kennebunk River curves through the landscape, bordered by trees. The property includes a serene setting with open spaces and distant houses visible among the greenery.
Home in Arundel

Classic, calm river view & centrally located home

KitchenFamilyCheck-in

4.95 out of 5 average rating, 107 reviews
Top guest favorite
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

KitchenIndoor spacesCheckout

4.98 out of 5 average rating, 42 reviews
Top guest favorite
A tranquil lake scene is captured at sunset, reflecting vibrant hues of orange and yellow in the water. Silhouettes of trees frame the horizon, while boats are moored along the shoreline. Soft ripples disturb the mirror-like surface of the lake.
Home in Middleton

Lake Living, sit back and relax!

Indoor spacesFamilyOutdoor spaces

5.0 out of 5 average rating, 21 reviews
Top guest favorite
Home in Milton

NH Lake House w/Private Beach, Hottub, & Lg Deck

FamilyKitchenCheck-in

5.0 out of 5 average rating, 50 reviews
Guest favorite
A charming red house, designed like a lighthouse, is nestled among lush trees by the water's edge. A screened-in porch is visible, alongside a wooden dock extending into the calm lake, reflecting the vibrant greenery surrounding the property.
Cottage in Lebanon

Casa de Luz - Lakefront 4 Bedroom Home

FamilyIndoor spacesAmenities

4.92 out of 5 average rating, 49 reviews

Family-friendly home rentals with a pool

Guest favorite
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

KitchenIndoor spacesWifi

4.91 out of 5 average rating, 286 reviews
Top guest favorite
A bright kitchen area features modern white cabinetry and a spacious countertop. Barstools with woven seats are positioned at the counter. Natural light floods in through a nearby door, illuminating the polished wooden floor and light blue walls.
Cottage in Wells

Cozy Cottage with Ocean Views, Wells Maine

Indoor spacesKitchenAccess

4.95 out of 5 average rating, 179 reviews
Top guest favorite
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

FamilyKitchenQuiet

5.0 out of 5 average rating, 100 reviews
Guest favorite
Home in Kennebunk

Beach House w/ Heated Pool · Fire Pit · Kennebunk

KitchenIndoor spacesCleanliness

4.83 out of 5 average rating, 179 reviews
Top guest favorite
Townhouse in Lincoln

Loon Views · 3BR King + Bunkroom

KitchenIndoor spacesPool

5.0 out of 5 average rating, 146 reviews
Top guest favorite
A welcoming entryway is framed by flowering shrubs and greenery. A small brick path leads to a light-colored door, accented by decorative lanterns. Potted plants add color, while a charming garden statue is positioned on the ground, contributing to the inviting exterior.
Guesthouse in Belmont

Charming Pool/Garden Guest House

FamilyKitchenCondition

4.98 out of 5 average rating, 254 reviews
Top guest favorite
The living area features a plush gray sofa and an armchair beside a large area rug. Natural light filters through a skylight, illuminating the space. A coffee table sits at the center, accompanied by two lamps and a faux fireplace, creating a cozy ambiance.
Condo in Ogunquit

Newly designed one-bedroom condo- heart of OGT

KitchenIndoor spacesAccuracy

4.97 out of 5 average rating, 105 reviews
Guest favorite
A modern kitchen displays sleek cabinetry and a white countertop with three wooden stools positioned at the bar. Open shelving holds decorative items and kitchen essentials. Natural light enters through a window, while a microwave and dishwasher are conveniently integrated into the design.
Vacation home in Gilford

Marty'sBay-RetroCondo, Private Beach, Concert Path

FamilyKitchenBeach

4.93 out of 5 average rating, 317 reviews

When is the best time to visit Milton?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$55,857 GYDG$56,694 GYDG$52,301 GYDG$57,949 GYDG$68,619 GYDG$84,100 GYDG$67,991 GYDG$72,803 GYDG$57,531 GYDG$56,485 GYDG$62,761 GYDG$61,506 GYD
Avg. temp-5°C-3°C1°C7°C13°C18°C21°C20°C16°C10°C4°C-1°C

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