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

Total vacation rentals
Explore 70 vacation rentals in Wakefield

Nightly prices starting at
Wakefield vacation rentals start at G$16,740 GYD per night before taxes and fees

Verified guest reviews
Over 2,530 verified reviews to help you choose

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
70 of Wakefield vacation rentals include wi-fi access

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

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

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.

Gorgeous Romantic Lakefront Getaway
Beautiful, 170 feet of waterfront Carriage House with a lovely sandy beach for a relaxing vacation in the Lakes Region of New Hampshire. Very close to the White Mountain National Forest, Kancamagus Highway, and several Ski Resorts. Within 45 minutes to the beaches of Maine and the Seacoast of New Hampshire. Our Carriage House is 1.5 hours from Boston and 2 hours from Worcester, MA. The Carriage House was built in 2021 with top-line finishes, fixtures, and furnishings for a romantic getaway.

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

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.

Pine River Pond
Directly on Pine River Pond, this 5-mile long, 570 acre lake has crystal clear water. This vacation rental is close to all of the area's most popular activities and ensures a memorable time! Swim in the summer, ice fish in the winter, numerous snowmobile trails or just get away from it all.This 1-bath property offers enough space to comfortably accommodate up to 10 guests, making it ideal for a family or group of close friends looking for an unforgettable New Hampshire lakeside retreat.

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.

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.

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.

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.

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!
Experience ultimate relaxation with over 100 feet of sandy lakeside beach frontage, nestled among serene pine trees. This spacious lake house features: Open concept main floor 3 levels (3100 sq ft) for privacy Family & dog friendly Hot tub, kayaks, beach, game room, firepit & more! Ideal for large families wanting to share a vacation without compromising on privacy. Enjoy year-round activities and create lasting memories. Get 10% OFF for weekly or longer stays!

Luxury Glamping NH - Geodome Sanctuary
Escape to a private luxury sanctuary retreat tucked behind a charming Christmas tree farm in Sutton, New Hampshire. This adults-only geodome features a private hot tub, wood-fired cedar sauna, cold plunge, and fire pit beneath a sky full of stars. Created for couples seeking rest, connection, and renewal, it’s the perfect place to slow down, reconnect, and experience the beauty of New Hampshire. Just 90 minutes from Boston, yet a world away.

Lake View Cottage / Fenced in Yard / Pet Friendly
Discover NH’s charm in our family-friendly cottage: Highlights: • Family and Pet-Friendly • Bright, recently renovated • Stunning lake views in a fantastic neighborhood Convenient Location: • Prime spot across from the lake • Use the boat launch for easy lake access Outdoor Adventures: • Ideal for fishing • Bring your own kayak or boat Winter Note: • Fenced yard may be inaccessible in winter.
Popular amenities for Wakefield family-friendly rentals
Family-friendly home rentals with a hot tub

Luxe Lodge in the Woods! With Sauna & Hot tub

Cozy Cabin on 5-acre Wooded Lot with Spa

The LOTUS welcomes you, stay a while

Luxurious Eagle Ridge Log Home at Newfound Lake

Sunny Waterfront Cottage at FarAway Pond

awesome private cabin

HotTub/5min to K-port, Pet friendly, @anchorunwind

Cozy Rock Cabin #thewaylifeshouldbe
Family- and pet-friendly home rentals

Tree House at the Shire

Tree Yurt

Secluded Mountain View Cabin • Private Sauna

Tranquil Pondside Retreat

In the Trees - NH w/ Lake Access

Cabin retreat just steps from adventure

Yurt on Chebeague Island

Mountain View Studio
Family-friendly home rentals with a pool

Basecamp in the White mountains

BC Fairytale cabin, hot tub, beach, trails

3 BR Cozy + Renovated Cabin in the White Mountains

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Million $ View of Lake Winni Flexible check in/out

Cozy, romantic cabin overlooking a stream - 24

Steep Falls Escape, river & falls just steps away

Loft Apartment on Tree-Lined Street in Falmouth
When is the best time to visit Wakefield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$58,800 GYD | G$64,659 GYD | G$46,036 GYD | G$46,663 GYD | G$60,474 GYD | G$65,078 GYD | G$80,562 GYD | G$79,516 GYD | G$63,822 GYD | G$63,822 GYD | G$58,591 GYD | G$57,335 GYD |
| Avg. temp | -5°C | -3°C | 1°C | 7°C | 13°C | 18°C | 21°C | 20°C | 16°C | 10°C | 4°C | -1°C |
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- Rentals with beach access Wakefield
- Waterfront rentals Wakefield
- Rentals with a kayak Wakefield
- Rentals with lake access Wakefield
- Rentals with a patio Wakefield
- Rentals with a fire pit Wakefield
- Rentals with a washer and dryer Wakefield
- House rentals Wakefield
- Pet-friendly rentals Wakefield
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- Beachfront rentals Wakefield
- Rentals with a fireplace Wakefield
- Family-friendly rentals Carroll County
- Family-friendly rentals New Hampshire
- Family-friendly rentals United States
- Sebago Lake
- Hampton Beach
- White Mountain National Forest
- Ogunquit Beach
- Wells Beach
- Squam Lake
- Story Land
- Weirs Beach
- Long Sands Beach
- Pats Peak Ski Area
- York Harbor Beach
- Willard Beach
- Loon Mountain Resort
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- Scarborough Beach
- North Hampton Beach
- Footbridge Beach
- East End Beach
- Cape Neddick Beach
- Tenney Mountain Resort
- Gooch's Beach
- Snhu Arena
- Cranmore Mountain Resort
- King Pine Ski Area





