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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 favourite
Apartment in Medford
5 out of 5 average rating, 6 reviews

ChicStylish Near Tufts/Boston 1BR w/ SitStand Desk

Located minutes from Tufts/Somerville, Cambridge, and Boston. This recently renovated flat offers a spacious, chic, open concept design with hardwood floors, lots of natural light, blackout shades, and glass markerboards. Modern kitchen equipped with stainless steel appliances and coffee machine. Stylish living room features a 65" flat screen smart TV, floating shelves, and adorable couch. Comfy bedroom offers a memory foam mattress, powered stand-up/sit-down Uplift Desk, and foldable treadmill.

Top guest favourite
Apartment in Billerica
4.99 out of 5 average rating, 176 reviews

Air Bee-n-Bee Hive– Unique Themed Creative Retreat

Plan a unique and memorable stay at the Hive, a bee-themed apartment in a Boston suburb 21.1 miles from the city. Delight in the charming honeybee-inspired décor. Relax on the patio and enjoy the nearby chickens and geese – and especially their fresh eggs. You’ll love the entertainment options – 100s of free movies plus cable TV and access to streaming channels. Everything you need is here, from a full kitchen with a coffee bar to EV charger. Got work? A workspace and super-fast Wi-Fi await you.

Guest favourite
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
4.94 out of 5 average rating, 33 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 favourite
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, 106 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.

Top guest favourite
The exterior of a Victorian home is showcased, featuring a light-colored facade with decorative trim. A welcoming porch area is accented by potted plants, and steps lead up to a wooden front door flanked by tall windows. Lush greenery surrounds the property.
Apartment in Newtonville
4.87 out of 5 average rating, 555 reviews

Country Charm minutes from the Hub - 1st Floor Apt

Private, smoke/pet-free 1st floor efficiency apartment with independent access for ONE PERSON ONLY at back of family home. Includes full bathroom, refrigerator, microwave, coffee maker + WiFi. All basic supplies provided. Driveway parking. Mins from MBTA transit including commuter rail. Laundry-room access for rentals of 7 nights ore more. Sorry, no vaping and no smokers - even if you smoke outside - because smoke odor on you or your clothes can be left in your wake in the room. No open flame.

Guest favourite
An outdoor shower is presented, featuring a wooden design with natural finishes. The shower head is positioned above a tiled wall, surrounded by potted plants that add greenery to the setting. Pebbles and gravel form the base, enhancing the outdoor ambiance.
Guest suite in Peabody
4.8 out of 5 average rating, 201 reviews

Cozy place to relax! 14min to Salem - 25 to Boston

Due to your allergies, we are unable to Host any animals Private entrance-Basement - H 6' - entrance 5' 6" Relax in this calm, stylish space after a day of exploration! Perfect for travelers /work trips. Stay with US! I live on-site to ensure a safe and welcoming stay You will get to enjoy: - Salem MA - - Boston MA - Beaches - Beverly MA - Gloucester MA - Marblehead MA - Trails Our mattress is fairly firm, which can provide a very good night sleep! - Illegal activities will be reported -

Guest favourite
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, 285 reviews

Home w/Yard+Parking & <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.

Guest favourite
A modern kitchenette is featured with stainless steel appliances, including an oven and refrigerator. A spacious gray sectional sofa is positioned on a geometric patterned area rug. Bright windows allow natural light to illuminate the room, complemented by decorative mirrors and a potted plant.
Apartment in Woburn
4.85 out of 5 average rating, 79 reviews

Newly Finished Guest Haven in Woburn

Welcome to our newly finished in-law lower level suite in Woburn! This private 1-king bed bedroom, 1-bath retreat features a cozy living room, a well-equipped kitchenette with a private entrance. Located on a quiet dead-end street, it’s just 5 minutes from Woburn Center, 15 minutes from Encore Boston Harbor, and a 20-minute drive to downtown Boston. Perfect for business travelers or couples, enjoy a peaceful stay with easy access to dining, shopping, and entertainment. Book your stay today!

Guest favourite
The spacious bedroom features a king-sized bed with a dark quilt and layered patterned bedding. Soft lamps provide ambient lighting on either side of the bed, which is set against a wall adorned with dark curtains. A flat-screen TV is positioned across from the bed, with an air conditioning unit nearby.
Guest suite in Melrose
4.92 out of 5 average rating, 566 reviews

Private Suite-Free Parking,near Boston Airp-Train

--> 7 miles N of Boston & a near subway, beaches, & airport (93, 95 & Rte 1), you’ll find the quaint city of Melrose. During 11/25 - 3/26 longer stay are possible. Please inquire. The Melrosian Suite is nestled behind other houses. Wake up to the chirping birds instead of Boston’s noise. 225 acres of ponds, trails & conservation lands are at top of street w/ distant views of Boston & the ocean. Before booking, check out info required when you book & house rules.

Top guest favourite
A spacious living area features a large, rounded red leather sofa surrounding a glass coffee table, complemented by a decorative area rug. Light-colored walls and recessed lighting enhance the bright atmosphere. Behind, a dining area with elegant chairs and cabinets is visible.
Home in Stoneham
4.97 out of 5 average rating, 31 reviews

The Grand Residence

Take it easy at this unique and tranquil getaway. The spacious living area in the basement,offering a serene retreat for relaxation . The cozy bedroom ensures a restful night’s sleep on comfortable bed. A fully equipped kitchen boasts premium appliances and everything you need to prepare delightful meals. Conveniently located near shopping center, restaurants . Perfect for business travelers, couples, or anyone looking to experience the finer things in life.

Top guest favourite
The historic colonial house is framed by blooming trees, showcasing a classic exterior in dark blue with white accents. A stone walkway leads to the grand entrance, featuring large windows and an inviting front door. The surrounding greenery enhances the home's stately appearance.
Apartment in Salem
4.99 out of 5 average rating, 169 reviews

The Salem House | First floor 2 bedroom apartment

Historic 1850 built colonial house with restored exterior and interior odes to Doric order architecture. Originally built for a leather factory owner named Thomas Looby, The Salem house is now a beautiful opportunity to visit Salem in a distinguished space. Exactly one mile from downtown with off street parking, staying here allows being away from the craziness of the city center while intimately experiencing Salem by staying in a historic colonial home.

Top guest favourite
A living room features large windows that allow natural light to fill the space, highlighting a blue sofa adorned with decorative pillows. A wooden coffee table sits on a patterned rug, complemented by a cozy chair and a small side table.
Apartment in Wakefield
4.98 out of 5 average rating, 97 reviews

Walk to train, lake and downtown - pets welcome

This is the perfect place to relax and make a home for your visit to the Boston area. You'll be steps from the park, Lake Quannapowit, shops and restaurants and the train station. The atmosphere is chill and relaxed. Upon arrival, you'll find coffee, tea, eggs and butter. If you're bringing your furry family member, there will be dog bowls and poop-bags too. Dog bed and cat litter box available upon request.

Popular amenities for Wakefield vacation rentals

When is the best time to visit Wakefield?

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Frequently Asked Questions

  • Do house rentals in Wakefield have free parking?

    Absolutely! We offer over 20 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 apartment rentals in Wakefield have air conditioning?

    Absolutely! We offer over 10 apartment 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 30 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 apartment rentals in Wakefield?

    Experience the best of Wakefield with our apartment rentals, starting at about $30 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 a kitchen, over 10 homes with air conditioning, over 10 homes with wifi, 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 $41 CAD 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 and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 of Wakefield vacation rentals include wifi 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!