Wakefield vacation rentals

4.99 out of 5 average rating, 128 reviews

A spacious deck features a circular table surrounded by six chairs, offering a view of the calm water. An oversized umbrella provides shade, while a barbecue grill is positioned at the back. The natural surroundings include trees in the distance.

Home in Wolfeboro

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.

4.99 out of 5 average rating, 88 reviews

Cottage in Wakefield

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.

4.99 out of 5 average rating, 135 reviews

Cottage in Acton

Eclectic Lakefront Cottage on Great East Lake

Welcome to a relaxing stay on the shores of Great East Lake. Swing in the hammock while listening to the cry of the loons. Or enjoy your morning coffee overlooking the quiet cove from your covered porch. 100 feet of shoreline in the calm 3rd basin of the lake. This entire basin is a "no-wake" zone which allows safe swimming for the whole family. Enjoy fishing, search for turtles, or explore beyond the cove using the canoe, kayaks, or paddle boards. Dock your own boat at the 24' aluminum dock.

4.96 out of 5 average rating, 303 reviews

A serene bathroom is displayed through a glass-paneled door, featuring a freestanding bathtub with a wooden mat beside it. Natural light filters through sheer curtains, illuminating the wooden panel walls and adding warmth to the space. A potted plant and neatly arranged toiletries enhance the calming atmosphere.

Guesthouse in Acton

The LOTUS welcomes you, stay a while

The Lotus is your zen home away from home. Enjoy peace and tranquility on your private back deck, the amazing salt water hot tub (exclusively use) new sauna (extra $88 per day) heated outdoor shower, deep bathtub (showering is tricky for people taller then 5'5)with bluetooth speaker.Comfortable king size bed with European bedding will let you get some much needed rest. Enjoy walks on our 12 ac property or any of the lakes near by for any kind of year round outdoor experience. Welcome :)

4.99 out of 5 average rating, 93 reviews

A quaint cottage is showcased under a blanket of snow, with holiday wreaths adorning the windows. Flanked by snow-laden trees, the structure exhibits a gabled roof and blue shutters, creating a charming winter scene.

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.

5 out of 5 average rating, 112 reviews

The modern guesthouse is shown against a twilight sky, featuring a sleek exterior in muted grey tones. Snow blankets the ground around the structure, while the entrance displays wide glass doors and a spacious balcony above. Lush greenery is visible in the background.

Guesthouse in Hiram

1BR cozy, luxurious getaway @ Krista's Guesthouse

Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

4.94 out of 5 average rating, 108 reviews

Spacious Belleau Lake House Amongst the Trees

You and your family & friends will feel right at home in this spacious custom built home in the tall trees across the street from beautiful Belleau Lake. There are three levels of living space, making it a great destination for small or mid sized groups or families looking to share a vacation without compromising privacy. It is also perfectly cozy for a couple. Enjoy the peacefulness of being high amongst the trees with the glow of the lake and shared sandy beach just steps away.

A wooden rack is mounted from the ceiling, displaying an assortment of clear glassware. Various types of glasses hang upside down, showcasing their elegant shapes and reflective surfaces, while soft lighting enhances the clarity of the glass.

4.96 out of 5 average rating, 96 reviews

Cozy Retreat-NEW Coffee Bar

Welcome to Buttercup Inn Tucked away in the peaceful lakes region, less than 2 miles from downtown Wakefield, this tastefully upgraded home may just surprise you. Every detail has been designed to make you feel right at home, from cozy furnishings to the brand new coffee bar- your go-to spot for a perfect brew. Whether you're unwinding or exploring the area, this charming retreat's proof that sometimes the best places are the ones you least expect. Message for further info.

5 out of 5 average rating, 38 reviews

A tranquil outdoor area showcases a pathway of stone pavers leading to a garden filled with blooming flowers. In the background, a rooster is seen roaming freely on the lush green grass, with a fence and open fields visible beyond.

Guesthouse in Wakefield

Peaceful Spring Retreat: Private Horse Farm

Gorgeous views from the big bay window. A nice 1 mile walking trail. A full kitchen to make homemade meals. A large TV to settle in and relax. A workspace if needed. Laundry. Extra space could be used for storage/air mattress/kid space. Come experience farm life and let us know if you want a visit with any of the animals. Horses, chickens & dogs. Our place is a perfect getaway for a couple or small family. Escape the busy city noise. Relax at our firepit and check out the stars

4.98 out of 5 average rating, 169 reviews

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, 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. Book now and get 10% OFF for weekly or longer stays!

5 out of 5 average rating, 204 reviews

A modern cabin with an A-frame shape is illuminated by warm lights, surrounded by tall trees. In front, a fire pit with wooden chairs invites gatherings, while a hot tub and sauna are visible nearby, contributing to the outdoor relaxation space.

Cabin in South Berwick

Romantic A-Frame cabin in the woods

Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

4.96 out of 5 average rating, 187 reviews

The lakeside house reflects beautifully on the calm waters of Sunrise Lake, enhanced by autumn foliage surrounding the property. The scene captures a warm glow from the setting sun, showcasing a serene and peaceful atmosphere by the water's edge.

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!

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Wakefield vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Wakefield

Superhost

A wooden dock extends over a calm lake, with two green kayaks tethered nearby. Lush greenery lines the water's edge, and distant hills are visible under a soft, overcast sky. Lily pads float gently on the lake's surface, creating a serene atmosphere.

Home in Newfield

4.91 out of 5 average rating, 43 reviews

Lakefront Retreat with Dock and Fenced in Yard

KristenRating, 5 stars1 month ago

This home was perfect for our family stay for a local wedding. It was a quiet relaxing place on the water! We enjoyed kayaking and sitting on the swing enjoying the view. The home included everything we needed and was very clean, spacious and comfortable. I would highly recommend this home to anyone looking in this area!

Superhost

Four blue Adirondack chairs are positioned on the shoreline of Province Lake, providing a tranquil view of the water. A small table beside one chair holds a cup and a notebook, inviting relaxation amidst the surrounding trees and gentle lapping of the lake.

Home in Effingham

4.86 out of 5 average rating, 44 reviews

Direct Lakefront. Swim/Fish/Kayak White Mountains

LynneRating, 5 stars4 months ago

We enjoyed our stay in the cute cabin. Since it was winter and we were mostly away from the cabin visiting family, we didn't get to take advantage of the lake and activities. But we enjoyed sipping coffee at the kitchen table and taking in the view of the frozen lake.

4.98 out of 5 average rating, 60 reviews

A teal bench is positioned against a white wall, complemented by a round, patterned area rug. On the bench, several decorative plates are arranged neatly. Next to the bench, a woven basket provides a place for storing small items.

Cottage in Wolfeboro

Relaxing Retreat in Historic Schoolhouse

PollyRating, 5 stars3 weeks ago

We love to stay here. Etoile is always very helpful and the place is clean. It is centrally located to where we want to be.

5 out of 5 average rating, 10 reviews

Lakefront Beauty with Private Beach

SanamRating, 5 stars1 week ago

This lake house was absolutely perfect. Well thought out, very organized, kitchen stocked with everything you might need for gourmet cooking (dishes, utensils, chef knives, various coffee pots, high end pans and serving ware etc), multiple options for seating areas, and of course lake stuff! We enjoyed having s’mores over a camp fire, bbq-ing, kayaking, paddle boating, and gaming. We enjoyed restaurants near and far - drove to Kennebunkport one day and Wolfeboro the next. We were comfortable in this spacious home. And the view topped off the experience. Even a rainy day brought inner calm looking out the windows. Highly recommend.

Superhost

A wooden deck is presented, surrounded by tall trees and offering views of the serene lake below. The deck's railing features metal wiring, providing a modern aesthetic while maintaining unobstructed sightlines to the lush surroundings.

4.88 out of 5 average rating, 16 reviews

Lakefront Retreat! Dog Friendly!

KimberlyRating, 5 stars9 months ago

This lake house was beautiful and the view is stunning! Every room is well appointed and perfect for setting a lake vacation vibe. The house has everything you could need. The description and pics on Airbnb are thorough and completely accurate. Jenna was an awesome host - very responsive and helpful and flexible. We will definitely be back!

A wooden staircase leads down to a serene lakefront, framed by tall trees. Clear water reflects sunlight, creating a peaceful ambiance. Colorful chairs are positioned along the shore, inviting relaxation by the water's edge.

4.79 out of 5 average rating, 52 reviews

Studio Lakefront Dog Friendly | Dock

SharonRating, 5 stars8 months ago

Pros: Very spacious for a studio Peaceful setting Several updates including kitchen and bathroom Clean Fireplace is a nice touch Good communication with host Cons: Slightly tricky check in directions (key code provided did not access lockbox in front of the home; though host was quick to respond with clarification that the correct lockbox is on the side of the home) Sloped, unpaved driveway was challenging for our rear wheel drive vehicle Landscaping is overgrown

5 out of 5 average rating, 21 reviews

An inviting fire pit is surrounded by four wooden Adirondack chairs, set on a grassy area surrounded by trees. Soft evening light creates a warm glow, and a stone ring encloses the fire, enhancing the natural setting.

Guesthouse in Wolfeboro

Sugar Hill Cottage Suite

ShawnRating, 5 starstoday

Casey & Katie have a beautiful home and family and it felt like we were a part of it for the stay. From the very moment we walked in to the second we left, all the little things they've added truly covered all our needs and we felt welcomed instantly. The space is beautiful and I'm sure it's great in every season , no matter the weather! Definitely will be booking again if I'm ever in the area for sure!

An outdoor dining set is positioned on a spacious deck, featuring a large table surrounded by six chairs. The backdrop includes tranquil lake views, with trees framing the scene. A soft, warm light glows from a lantern on the table, complemented by a setting sun.