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Wakefield vacation rentals

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Top-rated vacation rentals in Wakefield

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest suite in Lebanon

4.99 out of 5 average rating, 134 reviews

Rustic Rose Cottage of Historic West Lebanon

Rustic guest suite on serene four acres. Abutting colonial cape style house and West Lebanon Historic District date back to early 18th Century. Private parking & entrance, queen memory foam mattress, steam sauna, kitchen and laundry supplies, and desk and high speed wifi for telework. Minutes from Skydive New England, Prospect Hill Winery or McDougal Orchard. 30min to Portsmouth NH, Maine beaches, and Lake Winnipesaukee. Just over an hour to the White Mountains, Portland ME or the Boston area.

Farm stay in Alton

4.99 out of 5 average rating, 365 reviews

Treehouse Penthouse ❤ Beautiful inside & out

Kick back and relax in this calm, stylish apartment space. This space is an open concept with a king size bed. Lots of windows bring in natural light, cathedral ceiling and amazing view! A well-equipped kitchen/dining/living room combination that is great for short term or long term stays. Although there are other guest on the property you will have your own space to call your own and enjoy. Only 5 min from Lake Winnipesukee, 20 min to Wolfeboro, 25 min to Gunstock and 25 min to Bank of Pavilion

Cottage in Acton

4.99 out of 5 average rating, 112 reviews

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.

Guest suite in Lebanon

4.96 out of 5 average rating, 198 reviews

Maple Moon Farm, stay at a historic Maine farm! 1

Come and stay awhile! Unwind and enjoy a relaxing stay in our 1790’s farmhouse with many original features, situated on 120 mostly-wooded acres in southern Maine. Our farm features a commercial maple syrup operation, 200 high bush blueberry plants, a vegetable garden, pumpkin and berry patches, a variety of fruit trees, honeybee hives, miles of old logging roads for walks, skiing/snowshoeing, meandering brook, patio and outdoor fireplace, free-range chickens, and two large rescue farm dogs.

Guest suite in Wolfeboro

4.86 out of 5 average rating, 130 reviews

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!

Home in Lebanon

4.96 out of 5 average rating, 209 reviews

Tranquility, Relaxation, Family, Romance

Bring your family or have a romantic getaway in this beautiful 2 bedroom, 2 private baths located in this quiet country setting. Pet friendly. Big fenced in wooded back yard for your pets to roam. Big back yard deck w/ seating, grill. Minutes away to boat launching area to rent party boats, kayaks, paddle boats, Swimming, winter sports on Milton 3 ponds. Seasonal blueberry, peach, apple picking in town. Park your boat or snowmobile trailors. Skydive New England right in town. Fall leaves.

Guesthouse in Acton

4.96 out of 5 average rating, 265 reviews

The LOTUS welcomes you, your home away from home

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 :)

Cottage in Middleton

4.97 out of 5 average rating, 152 reviews

Beautiful Lakeside Cottage

Beautiful, quiet and secluded lakeside cottage. Enjoy amazing sunsets on our pristine lake. Swim, kayak, fish or just relax and take in the natural beauty. COVID UPDATE: We know everyone has different levels of concern regarding the virus. Please know that while we feel our sanitation and cleanliness of the Cottage is exceptional, we have doubled our efforts providing multiple cleanings between guests. This is a NON-SMOKING property. We are sorry, but we cannot accommodate pets.

Cottage in Parsonsfield

4.88 out of 5 average rating, 139 reviews

Riverpine Retreat - clean&bright waterfront home

Tucked away in a small town, minutes away from the New Hampshire border, located 2 minutes off of rt. 25 (direct route from Portland ME to NH) The ultimate family or couples getaway. Plenty of room in the back yard for any and all yard games, while also enjoying the firepit, "game shed" and 75ft of water frontage where you can swim, fish, or launch your kayaks from the dock into the Ossipee River. Wireless internet is available and reaches the back yard. The 'cabin' has 2 bedrooms.

Guesthouse in Hiram

5 out of 5 average rating, 101 reviews

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!

Home in Wakefield

4.93 out of 5 average rating, 105 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.

Cabin in Wakefield

4.97 out of 5 average rating, 237 reviews

Beautiful Log Cabin on Belleau Lake -2900 sqft!

Nestled among pine trees and with views of the lake it is the epitome of R&R. The log cabin is family & dog friendly with an open concept main floor; 3 levels of living space (2900 sq feet). Perfect spot for large families looking to share a vacation without compromising privacy, while also perfect for a getaway for 2! With year round activities for the whole family, it's the perfect place to create lasting memories! 10% OFF WEEKLY 7 NIGHT STAYS or more!

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Popular amenities for Wakefield vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Wakefield's top sights

Poor People's Pub33 locals recommend

Tumbledown Café23 locals recommend

Lovell Lake Food Center17 locals recommend

Miss Wakefield Diner & Gracie's Country Store16 locals recommend

Blue Bay Seafood & Steaks14 locals recommend

Knotty Pine Grill & Tavern12 locals recommend

Other great vacation rentals in Wakefield

Cottage in Wakefield

4.99 out of 5 average rating, 85 reviews

Gorgeous Romantic Lakefront Getaway

Home in Wakefield

5 out of 5 average rating, 27 reviews

Modern Lakefront Cabin (Pet Friendly, King Beds)

Home in Newfield

4.94 out of 5 average rating, 31 reviews

Lakefront Retreat with Dock and Fenced in Yard

Cabin in Wakefield

4.92 out of 5 average rating, 24 reviews

On Blueberry Hill

Home in Newfield

4.97 out of 5 average rating, 29 reviews

Peaceful 4 bedroom lakehouse retreat

Home in Wakefield

4.97 out of 5 average rating, 95 reviews

Getaway to the Lake. Just 30’ from the water.

Religious building in Shapleigh

5 out of 5 average rating, 44 reviews

Historic Schoolhouse c1866 / Pets OK / Hot tub

Home in Shapleigh

5 out of 5 average rating, 22 reviews

Luxury Lakefront Paradise with Private Beach

Quick stats about vacation rentals in Wakefield

Total rentals
90 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
2.7K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Wakefield?
Yes! Work meets play with ease at over 40 vacation rentals in Wakefield featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Wakefield?
Four-legged friends are welcome in Wakefield. Choose from more than 40 vacation rentals for guests traveling with pets.
Are there family-friendly house rentals in Wakefield?
Wakefield has more than 40 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do cottage rentals in Wakefield have a bbq area?
Absolutely! We offer over 10 cottage rentals with a bbq area in Wakefield. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in cabin rentals in Wakefield?
Experience the best of Wakefield with our cabin rentals, starting at about $180 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Wakefield have wireless internet?
Absolutely! We offer over 50 house rentals with wireless internet in Wakefield. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Wakefield have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in Wakefield. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Wakefield?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with a bbq area, over 40 homes with air conditioning, over 50 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

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