Vacation rentals in Wakefield

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Top-rated vacation rentals in Wakefield

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

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Guest favorite
A glass-paned door allows a view into a hallway leading to a well-lit kitchen. The hardwood floor extends into the space, and light fixtures along the ceiling provide illumination. Soft ambient light is seen towards the back, suggesting a welcoming atmosphere.
Apartment in Winchester
4.93 out of 5 average rating, 30 reviews

Winchester Apartment on Greenway

Updated apartment with hardwood floors, full kitchen and washer/dryer, next to Davidson Park, Tri-Community Greenway and the Community sport complex. A wonderful short walk down the Greenway takes you to Leonard Pond for tennis, pickleball, soccer or frisbee. A 20-minute walk down the Greenway takes you to Winchester Center for restaurants, shops and train to Boston. Or walk four blocks east to explore the 2,000-acre Middlesex Fells Reservation. Route 93 access is less than a 5-minute drive.

Guest favorite
A spacious bedroom features a large wooden bed dressed in light blue linens. A decorative area rug adds warmth to the hardwood floor. A full-length mirror stands against one wall, while a chair and a small plant complete the calming atmosphere. Natural light enters through the windows.
Apartment in Stoneham
5 out of 5 average rating, 8 reviews

Large 2-Bedroom 12 miles to Logan 10mile to Boston

Large 2BR in downtown Stoneham! Sleeps 6 with a king bed, full bed, and pull-out sofa. Enjoy a full kitchen, dining room, walk-in shower, in-unit washer/dryer, and AC. Hardwood floors throughout. Relax in the private yard with umbrella and table. Family- and pet-friendly, close to shops, restaurants, and just a short drive to Boston. Free street parking and Wi-Fi included—perfect for short or extended stays! Close to Boston with just 10 miles to Faneuil Hall and 12 Miles to airport 8to Everett.

Guest favorite
A comfortable living area is presented with a decorative tree adorned with lights. A faux fireplace sits beneath a flat-screen TV, complemented by a stylish coffee table. Light-colored furnishings and hardwood flooring enhance the inviting design, while a patterned area rug adds warmth.
Home in Wakefield
4.81 out of 5 average rating, 103 reviews

Beautiful home next to train to Boston, near Salem

Boston and Salem location, 3-story condo in two-unit building with its own entrance. Kitchen is brand-new, with a large bar area and all the appliances. One bedroom with a king-size bed is located on the main 2nd level. Two bedrooms upstairs, with one King bed and one Queen bed. It is located within walking distance to the Wakefield commuter rail with trains running into downtown Boston. Also, adjacent to a walkable park around a stunning lake, and a small downtown with stores and restaurants.

Guest favorite
A modern living area features a gray sectional sofa and an orange leather chair. A round wooden coffee table is centrally placed on a textured area rug. Mountain-themed artwork adorns the wall, while the kitchen is visible in the background with stainless steel appliances.
Apartment in Reading
4.89 out of 5 average rating, 18 reviews

Pet-Friendly Luxury | Near Boston + Parking

Experience comfort and convenience in this stylish one-bedroom apartment just minutes from Boston. Ideal for professionals and travelers, it features: - A king bed with crisp white linens. - A modern bathroom with a quartz countertop and stand-up shower. - A fully equipped kitchen and in-unit laundry. - Samsung Smart TV for streaming. - Pet-friendly accommodations. Enjoy building amenities like a gym and clubroom, secure parking, and easy commuter rail access. Perfect for business

Top guest favorite
A well-equipped kitchen presents stainless steel appliances and an island with seating for four. Natural light floods the space through large windows, creating a bright and inviting atmosphere. The adjacent sunroom is visible through an open entryway, enhancing the home’s spacious feel.
Home in Wakefield
4.96 out of 5 average rating, 281 reviews

Welcoming 7-room house <15 miles to Boston & Salem

Large kitchen (w/s.s. appliances & all the amenities), sun room, dining room, flat screen smart TVs in the living room & finished basement, high speed wi-fi (1gig) & laundry. Lots of windows make it bright. French doors open to a 16x16 deck leading to large fenced in yard. House is good for couples, business travelers, families, friends and pets. Close to downtown, train is a 5 minute walk away, highways, Lake Quannapowitt, Breakheart, 9 miles to Encore Casino & <15 miles to Boston & Salem.

Top guest favorite
A spacious living area features two couches, one in light blue fabric and the other in dark upholstery. A round wooden coffee table sits on a patterned rug. A wall mural depicts a serene landscape, while a television is mounted on the wall opposite a white shelving unit filled with books.
Guest suite in Stoneham
5 out of 5 average rating, 28 reviews

The Cottage Suite

Welcome to our private in-law apartment located in the basement of a family home. The clean and open concept apartment is fully equipped for a comfortable length of stay for you and your family. We are very close to the heart of Stoneham and STEPS to the local grocery store, pharmacy, restaurants, and ice cream shop. The nearest bus stop is a 2 min walk that will take you to Oak Grove Station in Malden which connects to the train station in Boston! If driving, I-95 and I-93 are minutes away!

Top guest favorite
The bedroom features a spacious bed with decorative pillows and a quilt. A bedside lamp and wooden furniture complement the room. Natural light enters through two small windows, and an art piece depicting Boston adorns the wall.
Apartment in Stoneham
4.99 out of 5 average rating, 121 reviews

Cozy Basement Apartment-Stoneham

This is a private in-law apartment in the basement of the home. Full Kitchen/living room combination, full bath and 1 bedroom with private entrance. Close to Routes 93 and 128 and 95. 15-45 minute drive to Boston depending on the traffic and time of day. Convenient to grocery stores and shopping plaza, casino. We live in the main house above the apartment. There is potential for a little overhead noise. Please read the whole listing and house rules. Must be 21 to request this listing!

Top guest favorite
A spacious bedroom features a wooden bed with neutral bedding and decorative pillows. A vintage guitar is displayed on the wall, while a potted plant adds a touch of greenery. Light streams in through a window with a view of the surroundings.
Private room in Arlington
4.94 out of 5 average rating, 342 reviews

Arlington Craftsman Green Room, Int. Well Restored

Private room, shared bath. The immaculate Interior of this classic craftsman has been lovingly restored. Bus stops are short walk. Bus is 15 mins. to Harvard Sq. Natural ponds nearby. NOTE: House Exterior is old, not yet restored. Fresh flowers, soft towels, high thread-count damask sheets. Simple breakfast: cereal, bread, fruit, coffee, tea, milk. Use of microwave & toaster. No oven/stove use. Note: It's 25 stairs to my front door +14 stairs to 2nd floor bedroom. No Pets, No Smoking.

Top guest favorite
Private room in West Somerville
4.9 out of 5 average rating, 181 reviews

compact room by Tufts Cambridge Davis Square 闪家@3

The compact room has a full bed and is on the second floor, cozy and sunny. The room has two windows with blinds and blackout curtains, oak wood floor, window AC in the summer, two bed end tables, two lamps with USB charge ports, walk-in closet with a laundry basket, a table with with two chairs, a mirror, and a tower fan that can make white noise. This bedroom shares a full bathroom with the other second floor bedroom and a ground level room, which are also rented through AirBnb.

Guest favorite
A bright studio space features a spacious bed with a light-colored blanket. Decorative wall art hangs above the bed, while a cozy seating area with a gray sofa and a coffee table is visible in the background. Natural light streams through nearby windows.
Apartment in Revere
4.92 out of 5 average rating, 188 reviews

Corner Cottage - cozy studio just north of Boston

Whether you’re a tourist visiting Boston for the weekend, a traveling nurse in search of a medium-term stay, or a pilot/flight attendant needing overnight accommodations, this completely renovated and professionally cleaned AirBnB is perfect for you! Finding living accommodations is tough; finding a reliable and responsive host is even tougher. Not only is this unit well equipped with almost everything you may need, but I will do my best to ensure your stay is the most comfortable.

Guest favorite
A well-appointed studio guest suite is shown, featuring a spacious bed with soft linens and natural light filtering through a large window. A small dining table with two chairs occupies one corner, while decorative shelves with woven baskets and books adorn the walls.
Guest suite in Peabody
4.97 out of 5 average rating, 224 reviews

Cozy West Peabody Guest Suite

Come enjoy this renovated studio guest suite in the quiet neighborhood of West Peabody! An easy drive to Salem or Boston, close to a woodsy bike trail, and a short drive to local shops and restaurants. Features a fully equipped kitchenette with a microwave and Keurig coffee. Make use of a Roku TV and fast, reliable WiFi to keep yourself entertained. This is a great space whether you are looking to explore the Boston North Shore or simply embark on a quiet getaway.

Top guest favorite
Private room in Melrose
4.89 out of 5 average rating, 123 reviews

B-Cozy/private parking/Walk T & BUS/Airport/Boston

Private room with one queen size beds, kitchenette with everything you need to make coffee, tea or a simple breakfast using the microwave, spacious living room with dining table. Only 6 miles from Boston, easy access to downtown by car or public transportation. One block to the commuter train station and bus station. 10 minutes walk to the metro station (orange line). Just a short walk to grocery stores, cafes and restaurants. Ideal for love or business travelers.

Popular amenities for Wakefield vacation rentals

When is the best time to visit Wakefield?

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Avg. priceR1,728 ZARR1,867 ZARR1,763 ZARR2,074 ZARR2,074 ZARR2,074 ZARR1,798 ZARR2,593 ZARR2,593 ZARR2,281 ZARR2,074 ZARR2,074 ZAR
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Frequently Asked Questions

  • Do house rentals in Wakefield have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Wakefield. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Wakefield?

    Four-legged friends are welcome in Wakefield. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do apartment rentals in Wakefield have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Wakefield. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Wakefield have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Wakefield. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Wakefield?

    Yes! Work meets play with ease at over 20 vacation rentals in Wakefield featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in house rentals in Wakefield?

    Experience the best of Wakefield with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for Apartment Rentals in Wakefield?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do apartment rentals in Wakefield have a kitchen?

    Absolutely! We offer over 10 apartment rentals with a kitchen in Wakefield. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Wakefield

  • Total vacation rentals

    Explore 40 vacation rentals in Wakefield

  • Nightly prices starting at

    Wakefield vacation rentals start at R519 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 2,490 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    40 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!