
Family-friendly vacation rentals in Winthrop
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Winthrop

Total vacation rentals
Explore 50 vacation rentals in Winthrop

Nightly prices starting at
Winthrop vacation rentals start at G$23,003 GYD per night before taxes and fees

Verified guest reviews
Over 1,240 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
50 of Winthrop vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winthrop rentals

4.9 Average rating
Winthrop stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated family-friendly rentals in Winthrop
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Off-Grid Cabin with Wood Fired Hot Tub. 4 Kayaks
Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- beautiful swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)
Indoor spacesFamilyParking

Moss House: A Modern Waterfront Cabin in the Woods
Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.
FamilyKitchenBreakfast

Quiet Lakefront Home, Private Dock!
Spacious four-season lakefront camp on peaceful Dexter Pond in central ME. Enjoy great fishing, canoeing, stand-up paddle boarding, kayaking, or relax and watch the sunsets and loons from the large porch overlooking the pond. The home is in a great location close to Winthrop Center and Wayne (10 mins to local grocery store/ farmers market) 30 mins to Augusta/airport. Many hiking trails nearby and lots of other areas to explore. It's beautiful in all seasons. Private dock, firepit, and laundry!
FamilyIndoor spacesSleep quality

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
Indoor spacesKitchenWifi

Carriage House
Renovated circa 1920 carriage house in a quaint New England college town. Eight-minute walk to busy downtown with restaurants, bars, shops, and grocery store. Elegant contemporary style. Open concept downstairs with sofa, daybed (napping in the sun!), and chef-designed kitchen. Second level with two queen beds and small balcony. Adjoins miles of walking trails and forest, full of wildlife. Less than 5-minute drive to a 1.5 mile running trail along the Sandy River, with refreshing swimming.
FamilyKitchenValue

Crow’s Nest Tiny House at Old Crow Ranch
The Crow's Nest Tiny House sits nestled on Old Crow Ranch, a 70-acre working livestock farm, a true example of thriving Maine farmland. You'll be surrounded by fields and pine woods in Durham, Maine. Just outside Freeport and only 30 minutes from Portland, this cozy space makes a calming retreat away from the city - for a night or for a week. Fall asleep listening to the peepers and gazing at the stars, drink your morning coffee while looking out at the cattle grazing in the fields.
Indoor spacesFamilySleep quality

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
FamilyIndoor spacesHiking

Near Beach+Cedar Sauna+Outdoor Shower+Pond+FirePit
Unwind at your own studio cabin with forest views, private sauna & pond! * New Private Cedar & Glass Barrel Sauna * Minutes to Reid State Park Beach & 5 Island🦞 * Fire Pit * Outdoor Shower * Rain Shower & Heated Bathroom Floor * AC/Heat * TV & Record Player w/Vinyl * Fast Wifi *Spruce Studio is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart & separated by a privacy screen and natural landscaping.
Indoor spacesKitchenSleep quality

Cozy, Efficiency Apartment with Hot Tub
Keep it simple at this peaceful, centrally-located efficiency apartment above our garage. 15 minutes to Gardiner/Augusta, 15 minutes to I95/295. Less than one hour from Portland. Sit by the stream, listen to the loons or enjoy relaxing in the hot tub. If you want to kayak, you can do that too! Eagles regularly soar overhead. Queen size bed, love seat and room enough for a pack and play. A/C, full kitchen, Keurig, microwave, toaster, dishes. Wifi and cable. Roomy parking.
FamilyIndoor spacesView

BREEZE, in a tree The Appleton Retreat
BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.
FamilyIndoor spacesOutdoor spaces

Large Private Waterfront Lakehouse in Maine
NEWLY RENOVATED! Direct waterfront on Lower Narrows Pond. Only 2.5 hours from Boston. Unwind on a pristine lake in Maine at this welcoming, completely private SPACIOUS lake house with over 2000 square feet of living space. Private dock, new winding staircase through the woods down to the dock, paddleboard, water trampoline, gas grill, and firepit. With 4 luxurious bedrooms including 2 king suites, this gorgeous property offers a retreat for the whole family.
KitchenFamilyBathroom

SkyView Treehouse | Lakefront • Private Hot Tub
Welcome to your dream treehouse escape — tucked among the pines with stunning lake views, a private hot tub, and direct access to Belgrade Stream. Designed for couples, honeymooners, and small families, SkyView Treehouse offers a luxurious retreat in nature. Enjoy starry nights in the hot tub, cozy evenings by the fireplace, and peaceful mornings on your private deck. Rustic charm meets upscale comfort in this unforgettable lakeside getaway.
FamilyKitchenAir conditioning
Popular amenities for Winthrop family-friendly rentals
Family-friendly home rentals with a hot tub

StreamSide Getaway- HOT TUB / AC/ Wi-Fi
FamilyIndoor spacesDecor

Cozy Rock Cabin #thewaylifeshouldbe
KitchenIndoor spacesLaundry

Hallowell Hilltop Home
FamilyKitchenAir conditioning

LuxuryTreehouse w/ Hot Tub Near Sunday River
Indoor spacesKitchenBathroom

Lakefront: Private Hot Tub, Sauna & Free Massages!
KitchenFamilyComfort

Roxie the Tiny Cabin on 100 acres
FamilyIndoor spacesQuiet

The Barnhouse with hot tub
FamilyIndoor spacesSleep quality

Cozy romantic A-frame by a woodland stream - 25
KitchenFamilyWifi
Family- and pet-friendly home rentals

Lakeside retreat on quiet cove on Cobbessee Lake!
KitchenIndoor spacesAccuracy

Mongolian Yurt on Chebeague Island
FamilyKitchenOutdoor spaces

Allie Mae Yurt nestled in the woods
FamilyKitchenSkiing

Downtown Augusta Studio - Newly Renovated #3
KitchenFamilyLong stay

Cabin retreat just steps from adventure
FamilyIndoor spacesQuiet

Jill's Place!
Indoor spacesKitchenGetting around

Lake house on Annabessacook
Indoor spacesFamilyHospitality

Lakeside Retreat
FamilyKitchenCondition
Family-friendly home rentals with a pool

Loft Apartment on Tree-Lined Street in Falmouth
Indoor spacesFamilyComfort

the lake house
Indoor spacesFamilyOutdoor spaces

Charming Saltwater Farm apartment
FamilyIndoor spacesLayout

Luxury Retreat In Back Cove | 10 Min to Downtown
FamilyIndoor spacesHospitality

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
Indoor spacesFamilyBathroom

Historic Schoolhouse c1866 + Pool + Lake + Hot tub
Indoor spacesKitchenTV

Farmhouse: Hot Tub, Mini Golf, Pickleball, POOL
Indoor spacesKitchenPets

Cozy 1 br condo with ski in/out lift access & Pool
Indoor spacesFamilyRiver
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$57,507 GYD | G$57,507 GYD | G$44,751 GYD | G$57,507 GYD | G$57,716 GYD | G$59,598 GYD | G$72,145 GYD | G$72,145 GYD | G$52,279 GYD | G$57,716 GYD | G$55,206 GYD | G$62,525 GYD |
| Avg. temp | -6°C | -5°C | 0°C | 6°C | 12°C | 17°C | 21°C | 20°C | 16°C | 9°C | 3°C | -2°C |
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- Sebago Lake
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- Coastal Maine Botanical Gardens
- Sunday River Resort
- Popham Beach State Park
- Pleasant Mountain Ski Area
- Wolfe's Neck Woods State Park
- The Camden Snow Bowl
- Rockland Breakwater Light
- Portland Museum of Art
- Maine Maritime Museum
- Bradbury Mountain State Park
- Bug Light Park
- Farnsworth Art Museum
- Grafton Notch State Park
- Reid State Park
- Camden Hills State Park
- Mt. Abram
- Cellardoor Winery
- Maine Lighthouse Museum





