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

Total vacation rentals
Explore 140 vacation rentals in Wolfeboro

Nightly prices starting at
Wolfeboro vacation rentals start at G$8,366 GYD per night before taxes and fees

Verified guest reviews
Over 4,970 verified reviews to help you choose

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
130 of Wolfeboro vacation rentals include wi-fi access

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

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

Tranquil Pondside Retreat
Welcome to this clean, bright, airy cabin with floor-to-ceiling windows and stunning views of Sargent's Pond in all seasons. At 62 acres and with just twelve homes, Sargent's Pond is the perfect place for simpler pursuits and peace and quiet. Enjoy two comfortable double bedrooms, a pull-out sofa in the living room, a bathroom with tub, washer, and dryer, a fully equipped kitchen with dishwasher, Wifi, bluetooth stereo system (bring your vinyl!), and Smart TV. Enjoy dining and relaxing on the spacious deck with commanding water views, and for the little ones, swinging and sliding on the swing set. Above the garage is a recreation room with a ping pong table as well as a smashing children's playroom filled with toys, board games, puzzles, and books. Enjoy the TV/ DVD player with a variety of favorite kids' flicks. Perfect for rainy days or down time, this extra living space is sure to please kids and adults alike! Please note that a pack-and-play, toddler mattress, and toddler high chair are available upon request.

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!

Luxury Year-round Hobbit House w/ private hot tub
Fern Hollow 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.

Caretakers Apartment-Split level w/ Wet Room Bath
Caretaker's Studio Apartment on the back of the Main House with a separate entrance. Enter on the first floor into a small living room with two chairs and Bathroom, climb 12 stairs up to kitchen/bedroom. The kitchen includes a sink, cabinets for storage, stove/oven combo and refrigerator open to the bedroom which includes a Double Bed is under the Elevated Loft with a Single Bed that is suitable for a child. The space is private and fully sound insulated. Guests can enjoy all of the common area

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.

Downtown, Cozy, Cute, and Convenient!
Walk just one block to the heart of downtown Wolfeboro, the "Oldest Summer Resort in America". Dine, shop, visit art galleries, or just relax in the park overlooking the docks on Wolfeboro Bay. Take the Mt Washington Ferry for a Lake Winnipesaukee ride or Molly the Trolley hop on/off tour. The rail trail is close by and a playground is just steps away for the little ones. Also, Wolfeboro’s best Mexican restaurant, coffee shops, Hunter’s grocery and Walgreens are all just a short walk away!

Pretty & Peaceful….close to Lake Winni!
Welcome to your Alton Bay retreat! Come relax & make lasting memories. Very clean, well stocked full kitchen & bath. Across the street is 200 acres of picturesque hiking trails & fishing. Turn left at the end of driveway and enjoy a scenic walk along Winni. Quiet location but close enough to Lake Winnipesaukee, Mt Major, Wolfeboro, Bank of Pavillion, boat launches, & docks, beaches, restaurants, shopping, sking, snowmobiling, boat rides, scuba diving, biking, kayaking, leaf peeping!

Lake Winnie Cozy Cottage Getaway
Welcome to Lake a Dream… your spot for a fun filled family vaca on Lake Winnie in the summer or a cozy couples getaway in the winter! With just a quick 3 minute walk from the property you can enjoy some sunshine & sand on the beach! Or a 5 minute drive into downtown Wolfeboro to experience it’s charm; waterfront dining, ice cream, shops, cafés & more! For winter stays, cozy up by the fireplace with a cup of hot cocoa & some fun family games! The cottage is not far from Gunstock & Kingpine!

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.

Writers Cabin in the Woods with Sauna!
Nestled in the woods and on Adams Pond with new wood fired sauna! The cabin feels totally hidden away but is less than 10 minutes to Bridgton and Naples, hiking, beaches and restaurants. The woods are beautiful and peaceful and the pond is just down a mossy path. Great for couples or a weekend away. Large deck with grill and outdoor shower, firepit. There is a shared dock on the pond for swimming, fishing, or just enjoying the view as well as a canoe and 2 kayaks, and a paddle board.

Sweet Apple Camp at Grey Shingles Camps
The Grey Shingles Camps property has been a cottage colony since the 1940's. After extensive renovations, our guests enjoy this historic property with a modern sensibility! The property has five acres of open lawn ,woodland, orchard, and private waterfront with sandy beach and docks on pristine Rust Pond. Amenities include kayaks, SUP's, canoes, sunfish; Pickleball, basketball, & more. The Rec Hall has a full kitchen, living room with cable TV, ping pong, foosball, & more!

Downtown Wolfeboro condo on Winnipesaukee w/Dock!
It's one thing to be right downtown in beautiful Wolfeboro, but add being right on the water w/your own porch, as you look over Wolfeboro Bay. Always something beautiful in front of you. This was my personal unit for a couple of years. It's fully equipped with a brand new bathroom lrg. tile shower, full kitchen, 55" UHD TV, Hi-Speed Internet, new Split System AC is comfy & quiet & a lrg. sectional couch that'll sleep-2 very comfortably. Lake living at its finest.
Popular amenities for Wolfeboro family-friendly rentals
Family-friendly home rentals with a hot tub

Tiny Riverfront A-Frame w/ Mountain Views, Hot Tub

The LOTUS welcomes you, stay a while

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

Cozy & Modern A-Frame in the woods w/HOT TUB

Million $ View of Lake Winni Flexible check in/out

Pet-friendly cabin with hot tub and beach access!

Luxurious Eagle Ridge Log Home at Newfound Lake

Troy’s Cabin: N. Conway w/ Hot Tub, A/C, Fireplace
Family- and pet-friendly home rentals

Waterfront on Opechee

The Little Red Retreat - No Adt. Cleaning Fee

Handcrafted A Frame near Newfound Lake and Hiking

Riverside Log Cabin Sanbornville NH

The Cottage on Paugus Bay- Lake Winnipesaukee

Log Home Meredith NH Pet Friendly Custom Fire-Pit

Secluded Cabin•Screened Porch•Near Loon

The Bear's Den: 40 acre Off-Grid Retreat +Gator
Family-friendly home rentals with a pool

Basecamp in the White mountains

3 BR Cozy + Renovated Cabin in the White Mountains

3 Bears Glen, Across St. from Story Land, AC, pool

Loon South Peak Riverfront 1Bd | Hot Tub & Pool

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

The Golden Eagle - Mountain Lodge

Mtn Views|Pools & Hot Tubs| Adventure Awaits

NEW! Mtn Views • Fireplace • Hot Tub • Pool Escape
When is the best time to visit Wolfeboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$54,382 GYD | G$55,009 GYD | G$51,872 GYD | G$52,290 GYD | G$54,173 GYD | G$62,748 GYD | G$67,768 GYD | G$65,467 GYD | G$57,101 GYD | G$56,473 GYD | G$59,402 GYD | G$60,029 GYD |
| Avg. temp | -5°C | -4°C | 1°C | 7°C | 14°C | 19°C | 22°C | 21°C | 16°C | 10°C | 4°C | -2°C |
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- Family-friendly rentals Carroll County
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- Family-friendly rentals United States
- White Mountain National Forest
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Story Land
- Squam Lake
- Weirs Beach
- Long Sands Beach
- York Harbor Beach
- Pats Peak Ski Area
- Loon Mountain Resort
- Scarborough Beach
- Mount Washington Cog Railway
- Willard Beach
- North Hampton Beach
- Short Sands Beach
- East End Beach
- Cape Neddick Beach
- Tenney Mountain Resort
- Franconia Notch State Park
- Gooch's Beach
- Omni Mount Washington Resort
- King Pine Ski Area
- Snhu Arena





