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Wakefield, MA vacation rentals
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Best Vacation rentals and Airbnb offers in Wakefield, MA

Our Favorite Family-Friendly Vacation Rentals in Wakefield, MA

The right family vacation rental in Wakefield, MA makes all the difference, keeping you close to top city attractions.

3br1.5ba Retreat - Near Airport - Wakefield, MA
9.8 22 reviews
Wakefield, MA
06/17 – 06/26
$1158/nighttotal: $10422 (9 )

3br1.5ba Retreat - Near Airport

3 4
apartment , Revere
This Revere condo is conveniently located 3 miles from Boston Logan Airport and 1 mile from Revere Beach.
This family-friendly dwelling accommodates up to 8 guests across 3 bedrooms and features a full kitchen, air conditioning, a washer/dryer, and a tranquil private garden with a Koi pond.
Stylish 1br In Assembly Square | Pool, Gym & Views - Wakefield, MA
10 3 reviews
Wakefield, MA
06/17 – 06/26
$429/nighttotal: $3861 (9 )

Stylish 1br In Assembly Square | Pool, Gym & Views

5 4
apartment , Somerville
This Somerville apartment is located downtown, a 5-minute walk from Assembly Row and LEGOLAND Discovery Center, with Assembly subway station just a 2-minute walk away.
This 600 sq ft dwelling accommodates up to 4 guests with 5 bedrooms and 1 bathroom, featuring a full kitchen, air conditioning, a swimming pool, garden with barbecue, and on-site billiards.
Luxe Everett 2br2ba W/ Pool, Gym & Parking - Wakefield, MA
10 1 review
Wakefield, MA
06/17 – 06/26
$512/nighttotal: $4608 (9 )

Luxe Everett 2br2ba W/ Pool, Gym & Parking

6 4
apartment , Everett
This Everett rental is centrally located, offering a 5-minute drive to TD Garden and a 7-minute drive to the New England Aquarium, with Chelsea Station a 14-minute walk away for regional travel.
This 900-square-foot unit accommodates up to 5 guests with 6 bedrooms and 2 bathrooms, featuring a full kitchen, air conditioning, Wi-Fi, a swimming pool, garden with barbecue, and on-site billiards.
Luxurious 2br - 2ba Apt At Hyatus - Wakefield, MA
9.6 21 reviews
Wakefield, MA
06/17 – 06/26
$617/nighttotal: $5553 (9 )

Luxurious 2br - 2ba Apt At Hyatus

3 4
apartment , Somerville
This Somerville apartment rental is conveniently located near Davis Square, Union Square, and Assembly Row, offering easy access to the Orange Line and I-93.
The 1000-square-foot unit features two bedrooms, two bathrooms, sleeps six, and includes a swimming pool, spa, and parking, plus modern amenities like a 65-inch smart TV and in-suite laundry.

Best Wakefield, MA vacation rentals with parking

19 Malden 3br Apt On 2f With Wifi And Free Parking With Windows Ac - Wakefield, MA
Wakefield, MA
06/17 – 06/26
$1732/nighttotal: $15588 (9 )

19 Malden 3br Apt On 2f With Wifi And Free Parking With Windows Ac

3 4
apartment , Malden
This 3-bedroom Malden apartment is located just a short drive from Cambridge College, Inman Square, and Boston North Station, making it a convenient base for exploring the city.
The 1,400-square-foot apartment features a fully equipped kitchen, free WiFi, and parking, and can accommodate up to 13 guests.
Beautiful 2 Bed Apt Minutes From Encore - Wakefield, MA
8.7 4 reviews
Wakefield, MA
06/17 – 06/26
$345/nighttotal: $3105 (9 )

Beautiful 2 Bed Apt Minutes From Encore

2 4
apartment , Everett
This Everett apartment rental is conveniently located near Encore Boston Harbor, just 3.1 miles from Boston's North Station and TD Garden, providing easy access to public transportation and major attractions.
This 750-square-foot, two-bedroom, two-bathroom unit sleeps six and includes a fully equipped kitchen with dishwasher, in-unit laundry, free Wi-Fi, air conditioning, parking, and a private entrance.
Beautiful 2 Bed Apt, Minutes From Encore - Wakefield, MA
Wakefield, MA
06/17 – 06/26
$307/nighttotal: $2763 (9 )

Beautiful 2 Bed Apt, Minutes From Encore

2 4
apartment , Everett
This Everett apartment is located an 11-minute walk from Encore Boston Harbor and a 5-minute drive from TD Garden.
This 750 sq ft unit accommodates up to 4 guests with 2 bedrooms and 1 bathroom, featuring a fully equipped kitchen, in-unit laundry, air conditioning, and on-site parking.
Sleek Somerville Apartment Near Encore! - Wakefield, MA
9.6 13 reviews
Wakefield, MA
06/17 – 06/26
$449/nighttotal: $4041 (9 )

Sleek Somerville Apartment Near Encore!

3 4
apartment , Somerville
This East Somerville apartment rental is conveniently located minutes from Encore Boston Harbor, Assembly Row, and Cambridge.
The 850-square-foot lower-level unit features three bedrooms, two bathrooms, off-street parking, a kitchenette with appliances (no stove), and accommodates up to six guests.

Frequently Asked Questions about vacation rentals in Wakefield, MA

  • What are the top family-friendly attractions in Wakefield, MA?

    The Wakefield Town Common is a great place for kids to run around and play. There's also a playground at the Greenwood School. For a more active outing, consider a visit to the Wakefield Memorial High School's athletic fields, which are open to the public.
  • What are the best Airbnb and vacation rentals in Wakefield, MA?

  • When is the best time to book a vacation rental in Wakefield, MA?

    The best time to book a vacation rental in Wakefield is during the summer months, when the weather is warm and sunny. You can also find good deals in the spring and fall, when the crowds are smaller.
  • What are the most popular Airbnbs in Wakefield, MA?

  • What events or festivals should visitors check out in and around Wakefield, MA?

    The Wakefield Farmers Market is held every Saturday from June to October. It's a great place to find fresh produce, baked goods, and other local products. The annual Wakefield Day celebration, held in August, is a fun event with live music, food vendors, and family activities.
  • What are the best rentals for families and kids in Wakefield, MA?

  • What are the best budget-friendly activities in Wakefield, MA?

    You can enjoy a free concert at the Wakefield Town Common during the summer months. The town also has a number of walking trails, which are perfect for a budget-friendly afternoon of exercise and fresh air. The library is another great option for free entertainment.
  • What are the best rentals or Airbnbs with a jacuzzi in Wakefield, MA?

    2 Bedrooms + Room For Crib/office - Perfect For Wfh and Get 2 *Winter* Discounts>long Stays For Family/wfh are the best vacation rentals or Airbnb with a jacuzzi in Wakefield, MA.

  • What are the best restaurants with local dishes in Wakefield, MA?

    The Corner Cafe is a popular spot for breakfast and lunch. They have a great selection of classic American dishes, as well as some local favorites. The Wakefield Tavern is a great option for dinner, with a menu that features fresh, seasonal ingredients.
  • What are the best walking or cycling routes in Wakefield, MA?

    The Lake Quannapowitt Loop Trail is a great option for a leisurely walk or bike ride. It's a 3.5-mile loop that goes around the lake. You can also check out the trails at the Greenwood School or the Wakefield Memorial High School athletic fields.
  • Are there pet-friendly attractions in Wakefield, MA?

    The Wakefield Town Common is a great place to walk your dog. There are also a number of dog parks in the area. You can find a list of pet-friendly restaurants and businesses on the town's website.
  • What are the benefits of choosing a vacation rental in Wakefield, MA?

    Vacation rentals can provide more space and privacy than a hotel. They are also often more affordable, especially for families or groups. You can find rentals in a variety of locations, from the heart of town to the quiet suburbs.
  • What are the top sports attractions and facilities in Wakefield, MA?

    The Wakefield Memorial High School has a variety of athletic facilities, including a football field, baseball field, and track. There are also a number of private sports clubs in the area.

Destinations nearby

Find the Best Vacation Rentals with Balconies in Wakefield, MA

Elevate your stay in Wakefield, MA with a vacation rental featuring a private balcony and stunning city skyline views.

Lux 3bd Minutes Walk To Airport - Wakefield, MA
Wakefield, MA
06/17 – 06/26
$523/nighttotal: $4707 (9 )

Lux 3bd Minutes Walk To Airport

3 4
apartment , Boston
This renovated East Boston condo offers exceptional proximity to Boston Logan International Airport, a 10-minute walk to the Blue Line subway, and convenient access to Downtown Boston, North End, Financial District, Boston Common, and Fenway Park.
This 1190 square foot residence accommodates up to 6 guests with 3 bedrooms, a fully equipped kitchen, air conditioning, a private balcony, and shared outdoor BBQ/dining space, all within walking distance of local restaurants and grocery stores.

Neighborhoods and points of interest in Wakefield, MA

Top Dog-Friendly Vacation Rentals in Wakefield, MA

Stay in a pet-friendly vacation rental in Wakefield, MA situated near dog parks and city walks, ensuring a comfortable stay for both you and your pet.

32 Nights Tax Free ! Getaway 4 - Wakefield, MA
9.8 189 reviews
Wakefield, MA
06/17 – 06/26
$292/nighttotal: $2628 (9 )

32 Nights Tax Free ! Getaway 4

1 4
apartment , Wilmington
This Wilmington apartment is just a short walk from the train station, offering easy access to Boston and its attractions. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The apartment has one bedroom and one bathroom, comfortably accommodating up to four guests. It features modern amenities like in-unit laundry, high-speed internet, and a spacious living area with a sleeper sofa. You can also enjoy the peaceful grounds and convenient parking.
Lux 2br In Assembly Square | Pool & Fitness Center - Wakefield, MA
10 4 reviews
Wakefield, MA
06/17 – 06/26
$704/nighttotal: $6336 (9 )

Lux 2br In Assembly Square | Pool & Fitness Center

6 4
apartment , Somerville
This 1050 sq ft, 6-bedroom, 2-bathroom apartment in Somerville offers easy access to Assembly Row shopping and LEGOLAND Discovery Center, located just a 5-minute walk from the Assembly subway station for convenient travel to Boston attractions like Encore Boston Harbor and Harvard Square.
This pet-friendly rental accommodates up to 5 guests and features a full kitchen, air conditioning, a swimming pool, garden, spa, billiard table, and in-unit laundry.
The Lantern On Beacon Hill - Wakefield, MA
Wakefield, MA
06/17 – 06/26
$1317/nighttotal: $11853 (9 )

The Lantern On Beacon Hill

1 4
apartment , Boston
This one-bedroom, one-bathroom apartment is situated in Boston's historic Beacon Hill, offering convenient walking access to the Charles River, Boston Common, and numerous shops and restaurants.
This entire unit accommodates up to 6 guests and is located near Fenway Park, The Freedom Trail, TD Garden, and Encore Boston Harbor, with pets allowed.
Peaceful, Modern 3br Home Near Encore Casino, 12min To Boston - Wakefield, MA
Wakefield, MA
06/17 – 06/26
$871/nighttotal: $7839 (9 )

Peaceful, Modern 3br Home Near Encore Casino, 12min To Boston

3 4
apartment , Everett
This renovated 3-bedroom house in Everett, MA, is located approximately 5 miles from Encore Boston Harbor Casino and 12 miles from Downtown Boston.
This pet-friendly rental accommodates up to 10 guests with 3 bedrooms, 1 bathroom, in-unit laundry, and off-street parking for two vehicles.
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