Wakefield vacation rentals

4.91 out of 5 average rating, 85 reviews

Cottage in Windham

Tranquil waterfront cottage

A private clean tranquil cottage, dock, parking, deck, grill, hammock, kitchen & all amenities, bathroom, 2 bedrooms, sleeps 5, futon, WIFI, cable, bidet, washer & dryer, granite outdoor table, kayaks, paddle boards, floats, fire pit and fireplace. Minutes from great restaurants, bars, hiking trails, and shopping. The most amazing sunsets. 30 minutes from Portland. Winter rentals as well. 40 min. from Shawnee Peek, 1 mile from Seacoast tubing. This place is privately yours. Smoke free please!

4.89 out of 5 average rating, 204 reviews

Condo in Kennebunk

Over 1000 Five Star Reviews! Walk to Dock Square !

Free onsite parking for 1 car. Beautiful coastal décor and modern amenities makes this a perfect choice for your vacation. Walking distance to EVERYTHING! Dock Square is a 1 minutes walk. Music, Art and Fine Dining surrounds you. Lots of windows and a slider to the deck make this location bright and airy 2 private decks for your enjoyment, two bedrooms, 2 full bathrooms. Perfect for couples or families. Parking for one car in lot, added public park across s NO PARTIES Pets considered

4.83 out of 5 average rating, 114 reviews

A welcoming cabin is situated down a gravel driveway surrounded by tall trees. Warm light spills from the windows, creating a cozy ambiance as dusk settles. A lantern beside the pathway adds a gentle glow, inviting guests toward the entrance.

Home in Conway

A Large Vacation Home with hot tub, game room +

My place is close to family-friendly activities, skiing, snowboarding, golf, shopping, hiking, restaurants, night life, shoe shoeing, ice skating, sleigh rides, tubing, Saco River tubing/canoeing, Echo Lake, Gondloa rides to summit, mini golf much more. You’ll love my place because of the quiet neighborhood, comfy beds, the kitchen, the hot tub and fireplaces and the space for large reunions and gatherings . My place is good for couples, business travelers, families (with kids), and big groups.

4.98 out of 5 average rating, 330 reviews

A wooden dock extends over vibrant green marshland, leading to a serene body of water. Lush trees and rolling grass create a peaceful backdrop, emphasizing the natural beauty of the surroundings.

Apartment in Arundel

Cape Arundel Cottage 1 mile to downtown KPT

Tastefully appointed 1 bedroom apartment one mile from desirable Dock Square, Kennebunkport. This apartment features Panoramic views of the famous Cape Arundel Golf Course and Goff's Brook Tidal River. Private, secluded back deck with dining and lounge areas, Cozy furnishings throughout, King sized bed with memory foam topper, Fully Equipped Kitchen, and more! At Cape Arundel Cottage, guest experience is our highest priority! *See “other things to note” for additional important information.*

4.94 out of 5 average rating, 126 reviews

Home in Windham

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

4.94 out of 5 average rating, 161 reviews

The exterior of a spacious mountain townhome is captured, featuring a warm wood façade and large windows that allow natural light inside. A deck extends from the front, overlooking a snowy landscape, with tall trees framing the serene setting.

Home in Carroll

Cozy Townhouse: Bretton Woods Mt. Washington Place

In the Mount Washington Resort (Bretton Woods) and near Cannon Mountain. Inviting four-season end-unit town home with warm ambiance, all the comforts you need, and great views. A mountain vacation getaway at a great value. Modern kitchen, comfortable dining and living room with fireplace. Four bedrooms, three floors, each with private bathroom (three full, one with shower). Large entertainment / recreation room for the family, outside deck with seating to enjoy the wildlife and a grill.

4.98 out of 5 average rating, 54 reviews

A fire pit surrounded by four wooden Adirondack chairs is set against a gravel area. The rustic lodge can be seen in the background, framed by trees displaying autumn colors and string lights. A peaceful and inviting outdoor space is highlighted.

Home in Jackson

The Sommet-Magical Views- Main house+Guest cottage

Welcome to The Sommet in Jackson, NH – a mountain getaway lodge - MAIN HOUSE with a GUEST COTTAGE. Picturesque views, local restaurants, and endless recreation await you at this 3-bedroom, 3-bath vacation rental! Located within minutes of Mt Washington, and the multiple ski areas. Mountain biking and hiking locations within minutes’ drive. Saco River provides outdoor recreation like canoeing, kayaking, tubing and rafting. Swimming, fishing could make this a perfect summer getaway.

4.85 out of 5 average rating, 350 reviews

A natural rock formation features small waterfalls cascading into a clear pool. Surrounding greenery adds a touch of nature, while guests are seen enjoying the water. Sunlight reflects off the rocks, creating a warm atmosphere.

Home in Conway

Private In Village, HotTub, 1 bedroom, Fire Place

PLEASE DO NOT BOOK PEAK HOLIDAYS/WEEKENDS IN ADVANCE as we try to rent the entire house 1st. We book this listing as a 1 bedroom ONLY. Directly in the village! yet tucked away, private YARD, HOT TUB, fireplace, new furniture, cozy beds and & linens. WALK to restaurants, Saco River, Golf, Village Green, Rec Center, Whitaker Woods, scenic train station, coffee shops, stores, skating, Cranmore & nightlife. Enjoy Kayaking, skiing, adventure parks, skiing, story land, hiking, etc.

4.96 out of 5 average rating, 78 reviews

A covered porch area is furnished with two white wicker chairs, accompanied by decorative pumpkins and colorful autumn leaves. String lights are draped along the railing, creating a welcoming outdoor space that invites relaxation in a residential setting.

Apartment in Northfield

The Lady Grand at Northfield

Comfy, Private, First Floor Appartment. Self Check-In, Parking New England vacation rental within walking distance to our scenic historic main street. Centrally located to bike parks, white water park, numerous skiing and hiking options. In an hour's drive, it is possible to be at the shore, in the mountains or one of our great cities! Our guest suite has a private entrance to a mud room and is fully furnished, full kitchen and bath and can sleep up to 6 people.

4.92 out of 5 average rating, 167 reviews

Condo in Lincoln

Cute Resort Studio Apt with Pool, hot tub at Loon

Relax with the whole family at this peaceful place to stay. Seated at the base of Loon Mountain’s South Peak, in New Hampshire's gorgeous White Mountains. Enjoy nature, hiking and lovely mountain scenery! Great area dining, and outdoor activities. Indoor pool and Jacuzzi are open and located in our facility. Great restaurants within walking distance. Free shuttle bus service to Loon Lift gate. Pemigewasset River in back.

Home in Old Orchard Beach

A small cabin features a welcoming front porch with two red adirondack chairs. The exterior is light-colored with blue shutters and a white door. A wooden ramp and steps provide access, surrounded by grass and shaded by trees, offering a comfortable entrance to the space.

4.86 out of 5 average rating, 14 reviews

Peaceful Sun and Fun Cabin-B

Your well needed relaxing and peaceful getaway awaits in this newly renovated cabin centrally located on a quiet safe street with short walk to the beach, restaurants, and Pier and amusements. This newly renovated 1-bedroom cozy cabin is perfect for a those looking to spend a peaceful and lovely time near the white sand in Old Orchard Beach. There is a hiking trail and biking trail beginning at the end of our street.

4.83 out of 5 average rating, 139 reviews

A bright dining area features a large glass table surrounded by six black wooden chairs. Natural light filters through three large windows, and a simple floral centerpiece sits at the table's center. A modern chandelier hangs above, complementing the neutral-toned walls.

Apartment in East End

Fall in LOVE With PORTLAND, MAINE

Portland and its surrounding areas is a FOODIE's paradise. Our comfortable home is perfect for Family or Friends to enjoy Portland's charm. Approx 3 miles from Portland Jetport and 90 miles from Boston Logan airport. Walk to downtown or the Old Port on the waterfront. The surrounding areas offer fine beaches and beautiful scenic towns guaranteed to make you want to come back and visit this best kept secret again!

Vacation rentals for every style

Get the amount of space that is right for you

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Popular amenities for Wakefield vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

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

4.99 out of 5 average rating, 68 reviews

An inviting exterior view of the property showcases a red house surrounded by lush greenery. String lights illuminate the outdoor seating area, which includes comfortable chairs and a hot tub, creating a serene atmosphere for relaxation.

Home in Thornton

70 Acre White Mountain Estate – Panoramic Views

Home in Old Orchard Beach

5 out of 5 average rating, 12 reviews

Stunning Beachfront Dream Home

4.93 out of 5 average rating, 58 reviews

A modern kitchen is highlighted with sleek white cabinets and a polished granite countertop. High-end stainless steel appliances, including a gas range, are featured. The open layout connects to a bright living area, where natural light fills the space through large windows.

Home in Scarborough

Gorgeous 4 BR home with HOT TUB

4.82 out of 5 average rating, 96 reviews

Home in Tamworth

Lakefront HotTub, Fireplace, Shop, Ski, Hike, Swim

4.97 out of 5 average rating, 63 reviews

Home in Gray

cozy 3 bedroom ranch with deck and screen porch

5 out of 5 average rating, 49 reviews

A spacious two-story house overlooks a lush green lawn, featuring multiple seating areas with wood chairs arranged around a fire pit. Large sliding doors open to balconies on both levels, providing views of the surrounding landscape and lake.

Vacation home in Tilton

Cheerful 4 bedroom, lake-front vacation home

4.92 out of 5 average rating, 179 reviews

A charming log cabin with a gabled roof is set against a clear blue sky. Large windows enhance the natural light and provide views of the surrounding trees. A spacious deck features outdoor seating, surrounded by stone steps leading to the lush green yard.

Cabin in Bartlett

Mountain View Retreat, Near skiing, shopping