Wakefield holiday rentals

We found 2,430 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other holiday rentals in Wakefield that are perfect for your trip. Holiday homes provide the best amenities for you and your friends, family or even pets, including parking and a garden. At the end of the day, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Wakefield

Showing deals for:25 Dec - 1 Jan

Interior
Private kitchen
Dining
Exceptional
(96 reviews)

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Boston

8% off
AU$16,761
for 7 nights, 1 home
AU$2,394 per night
includes taxes & fees
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Chestnut Sweet's front door on the garden. The Sweet is in its own building.
Terrace/patio
Interior
The garden
Exceptional
(156 reviews)

Charming private townhouse-style lodging, a block from Marblehead Harbor

Marblehead

8% off
AU$2,551
for 7 nights, 1 home
AU$364 per night
includes taxes & fees
Charming private townhouse-style lodging, a block from Marblehead Harbor
Living area
Living area
Outdoor dining
Room
Exceptional
(44 reviews)

Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH

Boston

8% off
AU$7,637
for 7 nights, 1 apartment
AU$1,091 per night
includes taxes & fees
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Sitting room
Property grounds
Exterior detail
Interior
Exceptional
(21 reviews)

Charming 2-bedroom house with a hidden garden in lovely Cambridge.

Cambridge

8% off
AU$4,692
for 7 nights, 1 home
AU$670 per night
includes taxes & fees
Charming 2-bedroom house with a hidden garden in lovely Cambridge.
Interior
Living area
Room
Exterior detail
Exceptional
(39 reviews)

Lovely Downtown Beverly

Beverly

8% off
AU$3,153
for 7 nights, 1 home
AU$450 per night
includes taxes & fees
Lovely Downtown Beverly
Interior
Exterior detail
Private kitchen
Living area
Exceptional
(34 reviews)

The Anchor House Marblehead Retreat - Minutes to Old Town and Historic Salem!

Marblehead

12% off
AU$4,866
for 7 nights, 1 home
AU$695 per night
includes taxes & fees
The Anchor House Marblehead Retreat - Minutes to Old Town and Historic Salem!
Living area
Living area
Property grounds
Room
Exceptional
(15 reviews)

Fresh Design-Walk to Salem-Food-Train Station

Beverly

8% off
AU$2,935
for 7 nights, 1 apartment
AU$419 per night
includes taxes & fees
Fresh Design-Walk to Salem-Food-Train Station
Dining
Living area
Tufts campus is just a 1 minute walk away with beautiful areas for sitting
Living area
Exceptional
(11 reviews)

Comfy, Stylish Apt. Near Uni's, Driveway

Somerville

8% off
AU$5,151
for 7 nights, 1 apartment
AU$736 per night
includes taxes & fees
Comfy, Stylish Apt. Near Uni's, Driveway
Exterior detail
Living area
Room
Private kitchen
Exceptional
(20 reviews)

Hocus Pocus Season is here! Don’t miss it!

Salem

6% off
AU$3,298
for 7 nights, 1 apartment
AU$471 per night
includes taxes & fees
Hocus Pocus Season is here! Don’t miss it!
Interior
Room
Dining
Interior
Exceptional
(45 reviews)

A Cozy 5BR Apartment near Harvard Square and MIT

Cambridge

7% off
AU$5,624
for 7 nights, 1 apartment
AU$803 per night
includes taxes & fees
A Cozy 5BR Apartment near Harvard Square and MIT
Dining
Exterior
Living area
Interior
Wonderful
(35 reviews)

Quiet neighborhood and Walking destination to Downtown Salem

Salem

15% off
AU$1,926
for 7 nights, 1 apartment
AU$275 per night
includes taxes & fees
Quiet neighborhood and Walking destination to Downtown Salem
Living area
Private kitchen
Room
Laundry in property
Exceptional
(52 reviews)

A beautiful 3BR Apartment near Harvard and MIT.

Cambridge

6% off
AU$4,152
for 7 nights, 1 apartment
AU$593 per night
includes taxes & fees
A beautiful 3BR Apartment near Harvard and MIT.
Exterior
Private kitchen
Living area
Room
Exceptional
(32 reviews)

Moody Salem Home Away From Home

Salem

8% off
AU$2,748
for 7 nights, 1 home
AU$393 per night
includes taxes & fees
Moody Salem Home Away From Home
Living area
Dining
Private kitchen
Outdoor dining
Exceptional
(42 reviews)

Samuel Tucker House - Downtown Luxury 2 Bedroom Condo

Marblehead

7% off
AU$2,768
for 7 nights, 1 apartment
AU$395 per night
includes taxes & fees
Samuel Tucker House - Downtown Luxury 2 Bedroom Condo
Private kitchen
Room
Living area
Terrace/patio
Exceptional
(24 reviews)

Cozy Cambridge 2bed 2bath w/ Patio & Parking Pass

Cambridge

16% off
AU$4,401
for 7 nights, 1 home
AU$629 per night
includes taxes & fees
Cozy Cambridge 2bed 2bath w/ Patio & Parking Pass
Room
Interior
Exterior
Interior
Wonderful
(15 reviews)

Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches

Winthrop

8% off
AU$1,955
for 7 nights, 1 apartment
AU$279 per night
includes taxes & fees
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
Modern kitchen with sleek cabinetry, ample counter space!
Step into the spacious living room complete with a Smart TV.
Exterior
Room
Exceptional
(7 reviews)

1803 Salem 1BR • Walk to Haunted Happenings

Salem

8% off
AU$2,777
for 7 nights, 1 apartment
AU$397 per night
includes taxes & fees
1803 Salem 1BR • Walk to Haunted Happenings
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.
.
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Exceptional
(68 reviews)

Family friendly home in historic Salem

Salem

8% off
AU$5,691
for 7 nights, 1 apartment
AU$813 per night
includes taxes & fees
Family friendly home in historic Salem
Room
Interior
Private kitchen
Dining
Exceptional
(55 reviews)

Beautiful Sunny Apartment in Salem

Salem

8% off
AU$2,821
for 7 nights, 1 apartment
AU$403 per night
includes taxes & fees
Beautiful Sunny Apartment in Salem
Living area
Exterior detail
Marina
Outdoor dining
Exceptional
(24 reviews)

Charming 1BR w/ Fireplace Near Fenway & Longwood

Brookline

8% off
AU$3,048
for 7 nights, 1 apartment
AU$435 per night
includes taxes & fees
Charming 1BR w/ Fireplace Near Fenway & Longwood
Interior
Living area
Living area
Property grounds
Exceptional
(29 reviews)

2 Story Stylish Gem- 3 bedroom 1 1/2 bath.

Boston

8% off
AU$5,321
for 7 nights, 1 apartment
AU$760 per night
includes taxes & fees
2 Story Stylish Gem- 3 bedroom 1 1/2 bath.
Living area
Private kitchen
Room
Dining
Exceptional
(19 reviews)

Beautiful 3BR+Office+Parking+Backyard near Boston-Cambridge.

Medford

8% off
AU$3,679
for 7 nights, 1 apartment
AU$526 per night
includes taxes & fees
Beautiful 3BR+Office+Parking+Backyard near Boston-Cambridge.
Dining
Interior
Queen size bed
Private kitchen
Exceptional
(38 reviews)

extended stays

Boston

7% off
AU$2,191
for 7 nights, 1 apartment
AU$313 per night
includes taxes & fees
extended stays
Interior
Marina
Interior
Living room, Instagram worthy!
Exceptional
(23 reviews)

Roomy Themed 3BR Historic Salem, Near Boston, with Parking, Walk to Attractions.

Salem

8% off
AU$4,599
for 7 nights, 1 apartment
AU$657 per night
includes taxes & fees
Roomy Themed 3BR Historic Salem, Near Boston, with Parking, Walk to Attractions.

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Friendly Wakefield will entice you

Enjoy the live music and other features of Wakefield. Travellers to this welcoming city praise the lake, restaurants and shopping. Fenway Park and Encore Boston Harbor are just a couple of the must-see attractions in the area. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Wakefield

Do you want to find attractions to see in the area? Venture out of your cosy holiday rental and experience everything that makes Wakefield a fun place to get away to. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Encore Boston Harbor (7.5 mi / 12.1 km)
  • LEGO® Discovery Center Boston (7.5 mi / 12.1 km)
  • Water Park of New England (8.3 mi / 13.3 km)
  • Bewitched in Salem (9.2 mi / 14.9 km)
  • New England Aquarium (10.1 mi / 16.2 km)
  • Boston Marathon Finish Line (10.7 mi / 17.2 km)

Exploring the natural landscape of Wakefield

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Wakefield is a great place to get outside. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Boston Common (10.3 mi / 16.6 km)
  • Boston Harbor (9.8 mi / 15.8 km)
  • Copley Square (10.6 mi / 17.1 km)
  • Glen Magna Farms (7.2 mi / 11.5 km)
  • Revere Beach (8.1 mi / 13 km)
  • Boston National Historical Park (9 mi / 14.6 km)

Transport to and around Wakefield

Fly into Beverly, MA (BVY-Beverly Municipal), the closest airport, located 9.9 mi (15.9 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Logan International Airport (BOS), which is 10 mi (16 km) away.

If you prefer train travel, make your way to Wakefield Station or Wakefield Greenwood Station and explore the city from there.

Frequently asked questions

What is the best area to stay in Wakefield when booking a holiday rental?
When considering a holiday rental in Wakefield, Massachusetts, the Lake Quannapowitt area stands out as an excellent choice. This picturesque neighbourhood is centred around the beautiful Lake Quannapowitt itself, which offers stunning views and a range of outdoor activities, including walking and cycling along the scenic pathways. The area is particularly popular for its tranquil atmosphere and proximity to nature.Another appealing option is the downtown Wakefield area, which boasts a charming blend of historic buildings and modern amenities. Here, you can explore a variety of local shops, cafes, and restaurants, making it a vibrant spot for visitors. The nearby Wakefield Cultural Council often hosts events and activities, providing a sense of community and entertainment.In terms of holiday rentals, Lake Quannapowitt offers a selection of properties, with options ranging from cosy lakefront cottages to more spacious family homes. Downtown Wakefield also features a range of accommodations, ensuring that visitors have ample choices to suit their needs.
Where are the best areas for renting a beach house in Wakefield?
For renting a beach house in Wakefield, consider the picturesque areas along Lake Quannapowitt, which offers a serene lakeside setting great for a relaxing getaway. Properties near the lake often feature amenities such as private docks, outdoor seating areas, and spacious backyards, making them ideal for gatherings or family retreats. Many homes also come equipped with modern kitchens and barbecue facilities, allowing guests to enjoy al fresco dining while taking in the scenic views.Additionally, the nearby Horn Pond area presents more options for visitors seeking a beach house experience. Here, you can find properties that provide easy access to walking trails and picnic spots, along with amenities like fire pits and outdoor grills, great for evening relaxation. The community vibe in these neighbourhoods is welcoming, with local shops and cafes just a short drive away, adding to the convenience of your stay.For those interested in exploring the broader region, the proximity to the North Shore beaches, including places like Lynn and Swampscott, offers additional options for sunny days by the ocean.
What is the most popular type of holiday rental accomodation in Wakefield?
In Wakefield, holiday houses are the most popular type of holiday rental, with about 12 available in the area. These properties typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Additionally, several condos and apartments can be found, providing travellers with more compact living options. These rentals often come with amenities such as laundry facilities and access to communal spaces, ensuring a comfortable stay.
Are there any family house rentals in Wakefield?
In Wakefield, Massachusetts, there are several family-friendly house rentals available, making it an appealing destination for those travelling with children. The town offers a variety of spacious homes, often complete with multiple bedrooms and ample living space for families to relax together. Many properties feature full kitchens, enabling guests to prepare meals at their convenience, as well as outdoor areas for children to play.Visitors will find themselves near local parks, such as Lake Quannapowitt, which is superb for family outings with its walking trails and playgrounds. Additionally, the charming downtown area is just a short drive away, where families can explore shops, cafes, and community events.
Are there pet-friendly house rentals in Wakefield?
In Wakefield, there are several pet-friendly house rentals available, making it a welcoming destination for travellers with furry companions. Many of these properties feature amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, allowing for a home-like experience during your stay.The town itself offers a charming environment with access to various local parks, ideal for walks with pets. Lake Quannapowitt is a popular spot nearby, featuring walking trails and scenic views, great for enjoying leisurely afternoons outdoors. Additionally, Wakefield's proximity to Boston means that visitors can easily explore the city while returning to the tranquillity of a pet-friendly rental in this lovely suburban area.
Are there any remote work holiday rentals in Wakefield?
In Wakefield, Massachusetts, there are approximately 18 remote work-friendly holiday rentals available. This charming town offers a variety of accommodations that cater to travellers looking for a productive environment. Many properties feature dedicated workspaces with desks and comfortable chairs, ensuring that guests can work effectively during their stay.Furthermore, most rentals come equipped with free Wi-Fi, allowing for seamless connectivity. The town itself is a lovely area, known for its picturesque Lake Quannapowitt, where you can enjoy a stroll or a jog during breaks. Additionally, the local amenities include cafes and restaurants, providing convenient options for meals and refreshments. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Wakefield?
In Wakefield, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals. Many properties also feature coffee and tea makers for a convenient caffeine fix. Decks or patios are common, providing outdoor space to relax and enjoy the surroundings. Onsite parking is typically available, making it easy for guests with vehicles to explore the area. Additionally, many rentals offer dedicated desks, suiting those who may need to work or study during their stay.
When is the best time to visit Wakefield for a holiday rental?
The peak season in Wakefield runs from May to July, with July being the most popular month for visitors. This vibrant period attracts those looking to enjoy the warm weather and outdoor activities, such as kayaking on Lake Quannapowitt or exploring the scenic parks that dot the area. The pleasant temperatures, typically ranging from 18 to 30 degrees Celsius, create an inviting environment for sightseeing and leisurely strolls along the waterfront.If you prefer a quieter experience while still enjoying the charm of Wakefield, consider visiting in December. This month offers a unique opportunity to appreciate the town's festive atmosphere as holiday decorations illuminate the streets. Although it's the low season, you'll find that the local community spirit is vibrant, and there are often seasonal events that provide delightful experiences without the usual crowds.
What are the top attractions in Wakefield?
In Wakefield, Massachusetts, visitors can enjoy a variety of attractions that highlight the town's charm and natural beauty. Lake Quannapowitt is a central feature, offering scenic walking paths and opportunities for outdoor activities such as fishing and boating. The nearby Wakefield Common is a lovely park great for picnics and leisure, often hosting community events throughout the year.Cultural enthusiasts might appreciate the Wakefield-Lynnfield Chamber of Commerce Art Gallery, which showcases local artists and hosts exhibitions. The town's historic district is also worth exploring, featuring beautifully preserved architecture that reflects Wakefield's rich history.
Are all fees included in the Wakefield holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Wakefield holiday homes with parking?
Stayz offers a wide selection of holiday homes in Wakefield with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Wakefield holiday homes?
You can find great discounts on holiday homes in Wakefield on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Wakefield holiday home booking on Stayz?
To find Wakefield holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Wakefield?
A long-stay holiday home in Wakefield is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Wakefield holiday home?
Book your Wakefield holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Wakefield?
Prices for holiday homes in Wakefield vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Wakefield to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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