
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$23,005 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)

Lakefront: Private Hot Tub, Sauna & Free Massages!
Make memories at our updated, 2500 sq. ft., lakefront home. Use our kayaks, canoes & peddle boats for the family! Great fishing - 648 acre lake. We offer many outside games, range of indoor games & arcade systems. Amazing 4-seasons room with outdoor dining setup viewing the lake. Enjoy our new hot tub, and grilling deck right outside master bedroom. Lavish soaking tub in master bath. Only 4 minutes to golf, 10 minutes to capital city, Augusta, and 45 minutes to skiing as well as Atlantic Ocean!

Privacy, River, Pond, A frame Hot Tub, EPIC Views,
14 Acres Secluded A-frame nestled along Clean Crooked River, Hot tub with breathtaking VIEWS and world-class fishing. Swim in the river, private pond or explore hiking trails right from your door. Central AC - Gas Fireplace - Modern Kitchen. Just minutes from pristine lakes, primo golf courses, and thrilling ski slopes, this charming private oasis offers an ideal mix of tranquil relaxation and outdoor adventure. Invite a private chef, florist or yoga teacher to fully unwind. Heated bath floors.

Quiet Lakefront Home, Fall dates open!
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, a/c, laundry!

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

Mirror Pond Cottage
A sweet space on a pond, this cottage is perfect for those looking for a quiet getaway. We offer swimming, kayaks and a canoe, life jackets along with a raft to float on. Endless fun in the water, with no motors to be heard. This is a quiet spot and we would hate to be responsible for ruining that. We are family friendly and kids are welcome, but please leave the party at the casino (5 minutes away)! The waterfront is sandy and shallow, perfect for young ones to splash around in.

Solar Powered Bus in Forest | Hot Tub + Wellness
Imagine waking up in a hand-painted, solar-lit bus surrounded by beautiful trees, birdsong just outside the window, and 110 acres of forest trails waiting at your door. A one-of-a-kind stay tucked into 110 acres of balsam fir forest at Celebration Tree Farm Wellbeing Center. Private saltwater hot tub included. Art supplies, yoga mats, wellness offerings, and peace & quiet await you. Your stay directly supports a living mission of earth connection, community, and personal renewal.

Lakeside retreat on quiet cove on Cobbessee Lake!
Nothing beats summer days on the lake in Maine. Not only is this lake home situated on a quiet cove on central Maine's Cobbossee Lake, but it is near amenities in Augusta and close to I-95! Enjoy two large docks, a large lawn and gently sloping swimming area, and a newly renovated five bedroom house with two full bathrooms. This is the Maine vacation home you are looking for! Two of the bedrooms and one bathroom are in the basement, which is still under some small construction.

The Maine Frame | Modern A-Frame Cabin in Freeport
• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

Charming Cottage With Spectacular Water View
Find peace and serenity as you gaze at the glistening waters of the Sheepscot River. Our property sitting on Davis Island in Edgecomb, Maine overlooks the quaint town of Wiscasset, providing a calm atmosphere, stunning evening sunsets, and panoramic views. Located within the Sheepscot Harbour Village Resort, you are in a prime location to have access to local shops, antique markets, and restaurants. Take a stroll down to the Pier where you can experience the water up close.

Price's Point - Cabin on the water
Brand new Cozy Cabin on a small 181 acre pond. Enjoy the cabin feel of knotty pine and a big country porch overlooking the water. Walk in access to the water or ice in the winter. Kayaking, canoeing, ice fishing, snowmobiling and more depending on the time of year. A peaceful location a mile down a private road but 10 minutes away from a grocery store etc. Eagles, loons and fish will be your neighbors as you are in the moment at Price's Point.

Private Lake House, Firepit & Amazing Sunset Views
Spring & summer at Lakeshore Point, a private lakefront home on Canton Lake in Maine. Privately set at the end of a quiet lane, this updated modern retreat offers 200’ of pristine waterfront and your own private sandy shoreline. Swim, kayak, and paddleboard by day, then gather around the fire pit at sunset. Thoughtfully designed with a full kitchen, WiFi, and outdoor shower, it’s where family adventure meets relaxed lakeside New England charm.
Popular amenities for Winthrop family-friendly rentals
Family-friendly home rentals with a hot tub

The Loons' Nest: Lakefront oasis w/ hottub

Cozy, Efficiency Apartment with Hot Tub

LuxuryTreehouse w/ Hot Tub Near Sunday River

The Modern Lakehouse

Cozy Rock Cabin #thewaylifeshouldbe

Modern Treehouse w/Water Views+Cedar Hot Tub

Log cabin, stunning views, hot tub, fire pit

Waterfront,Hot tub,Private dock,Freshly renovated
Family- and pet-friendly home rentals

Studio Apartment in Freeport

Visit Beautiful Home on Snow Pond

McKeen's Riverside Retreat

Lakeside 3 BR Cabin in Boothbay Harbor

Farm house, River, Island, animals & private Chef.

Camp Bai Yuka/Little Camp (Log Cabin on Webb Lake)

Simple Boothbay Log Cabin on Water

Lakefront Home w/ Dock | Porter Lake | Sugarloaf!
Family-friendly home rentals with a pool

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

the lake house

Farmhouse: Hot Tub, Mini Golf, Pickleball, POOL

Luxury Retreat In Back Cove | 10 Min to Downtown

Loft Apartment on Tree-Lined Street in Falmouth

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

Apt in Victorian Mansion w/ Hot Tub, Parking, Pool

Resort-like 2 bed/1 bath - seasonal pool/hot tub
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$57,513 GYD | G$57,513 GYD | G$44,756 GYD | G$57,513 GYD | G$57,722 GYD | G$59,604 GYD | G$72,153 GYD | G$72,153 GYD | G$52,285 GYD | G$57,722 GYD | G$55,213 GYD | G$62,532 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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- Mt. Abram
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