Vacation rentals in Wakefield

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Top-rated vacation rentals in Wakefield

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Guest favorite

Guest suite in Winchester

5.0 out of 5 average rating, 102 reviews

Warm and cozy 1st flr sweet guest suite w parking

Easy living at this peaceful and centrally-located guest suite. Winchester is the quintessential New England town located just 8 miles from Boston with an easy drive or 16 minute by train from Winchester Center or Wedgemere. Or check out historic Lexington and Concord next door, bustling Arlington Center or hip Davis Square. Tufts University, Harvard Square, Harvard University and MIT nearby. Your comfortable home away from home for fun excursions, get aways, business meeting or college visits

Mar 30 – Apr 6

G$21,032 GYD per night

Guest favorite

Guest suite in Peabody

4.95 out of 5 average rating, 552 reviews

PRIVATE, LARGE COUNTRY STYLE SUITE

LARGE ground floor apartment with your own entrance. Master Bedroom has: . Half bath . Queen size bed. . Full size sofa bed . TV/Netflix . Cozy gas burning heating stove . Desk/chair . Water cooler . Coffee/Tea Kitchen includes . Sink . Big Refrigerator . Microwave . Induction stove tops . Toaster Oven Living Room . Queen Sofa Bed . 2 Recliners . 50" TV Laundry Room Full Bathroom Shopping plaza 2 miles down the road and just 5 minutes to I- 95 or Rt. 1 and only 20 minutes to Boston or Salem.

Mar 14 – 21

G$30,971 GYD per night

Guest favorite

Apartment in Woburn

4.96 out of 5 average rating, 105 reviews

Comfy-Spacious-private 1BR conveniently located

This stylish, private place is perfect for a couple or a small family. Conveniently located minutes from Boston or the north shore whether you are traveling by car, Uber, or local train. Enjoy Boston adventures, north shore excursions, beaches, fall leaf peeping, skiing, historical visits to Massachusetts battle grounds, or some retail therapy at shops and malls nearby. An array of local and city restaurants and breweries provide a multitude of options for your pleasure. YMCA just steps away!

Jan 21 – 28

G$28,047 GYD per night

Guest favorite

Guest suite in Burlington

4.98 out of 5 average rating, 202 reviews

Relaxing 2 Room Suite with Private Bath/Deck/Patio

Welcome to this spacious, quiet and relaxing furnished suite (private entrance own deck- patio-fire pit). It is truly in an amazing location; walking distance to Mall/Lahey Hospital & only 18 mi from Boston Logan Airport, with plenty of parking. Our place is good for professionals, students, couples, solo, families (with kids). The airbnb is attached to a main house but it's contactless (check-in/-out) with own entrance. Ideal for 2, a little tight for 3 but manageable (sofa into bed).

Nov 11 – 18

G$20,237 GYD per night

Guest favorite

Home in Wakefield

4.96 out of 5 average rating, 208 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.

Jan 9 – 16

G$70,032 GYD per night

Guest favorite

Apartment in Salem

4.97 out of 5 average rating, 300 reviews

The Salem House Too

An 1850’s built home with a modern interior and revitalized exterior. It’s the perfect spot to relax and unwind or take work on the road. Located one mile from downtown Salem and away from the traffic, our goal is to provide a classy, upscale experience with all of the comforts of home. Pair a sparkling clean private space with off street parking, unlimited coffee, and a fridge stocked with drinks and snacks and you’ve got The Salem House! Come stay with us and see what Salem is all about!

Feb 9 – 16

G$27,521 GYD per night

Guest favorite

Guest suite in Peabody

4.98 out of 5 average rating, 177 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 and an outdoor space with a fire pit and charcoal grill. 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.

Aug 12 – 19

G$23,215 GYD per night

Guest favorite

Guest suite in Melrose

4.84 out of 5 average rating, 240 reviews

Guest Suite with separate entrance

Guest Suite with open floor plan (kitchen with stove/oven, refrigerator, microwave, bottled water dispenser); living area (pullout couch, loveseat, 50" TV with Roku and Netflix); sleeping area, bathroom with shower, separate entrance, 1 off-street parking space. Convenient to public transportation (commuter rail - 5 min walk, 12 min ride to Boston/45 min ride to N Shore; subway - 2 min walk to bus/subway (25-40 min ride to Boston) or drive (25-45m to Boston or 45-60m to N Shore).

Nov 9 – 16

G$23,315 GYD per night

Guest favorite

Guest suite in Melrose

4.93 out of 5 average rating, 488 reviews

Private & Cozy Suite -near Bost-Airp-Salem-Train

7 miles N of Boston & a near the subway, beaches, airport & Salem (93, 95 & Rte 1), you’ll find the charming city of Melrose. The Melrosian Suite is nestled behind other houses & surrounded by gardens and trees. Wake up to the sounds of chirping birds instead of Boston’s noise and congestion. 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.

Aug 16 – 23

G$21,539 GYD per night

Guest favorite

Home in Lynn

4.91 out of 5 average rating, 226 reviews

Clean, spacious In-Law Suite -Near Everything

Immaculately furnished, clean and spacious In-Law Suite features: 1 bedroom, 1 full bath, dining kitchen, and living room located steps from Lynn Woods Reservation (over 30 miles of picturesque New England trails perfect for hiking, running, mountain biking and cross-country skiing) and short drives from beaches, Boston and North Shore. Kids toys, a baby crib and access to a large beautiful upstairs deck and bbq are available upon request.

Nov 14 – 21

G$30,386 GYD per night

Guest favorite

Guest suite in Peabody

4.94 out of 5 average rating, 196 reviews

Cozy NorthShore Suite Close to SALEM, MA

Welcome to @TheCozyNorthShore! Our modern basement apartment offers a private entrance, queen bed, kitchenette, and bathroom. Ideal for couples, solo adventurers, or business travelers. Conveniently located, less than an 8-minute ride from downtown Salem. *Note: We are a family of 4 that lives in the main area upstairs, and you will likely hear us. But we’ll do the best we can to keep the noise down and let you enjoy the space*

Jul 7 – 14

G$31,653 GYD per night

Guest favorite

Guest suite in Medford

4.92 out of 5 average rating, 123 reviews

Beautiful 1 Bedroom, 1 Bathroom in Medford

Come stay in this recently renovated, very comfortable space situated in a quiet neighborhood across the street from the Brooks Estate woods, just outside of Boston. The house itself is a historical gothic cottage built in 1856 and is the 2nd oldest home in the area. The space is in a historic single family home and both the bedroom and bathroom are 100% PRIVATE and separated from the rest of the house with a private entrance.

Jan 5 – 12

G$23,415 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Wakefield vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Wakefield's top sights

Jordan's Furniture Reading6 locals recommend

Iron Town Diner3 locals recommend

IMAX 3D Theater at Jordan's Furniture Reading6 locals recommend

Greater Boston Stage Company3 locals recommend

Brothers Deli Restaurant4 locals recommend

Blue Moon Grill7 locals recommend

Other great vacation rentals in Wakefield

Guest favorite

Home in Billerica

4.97 out of 5 average rating, 151 reviews

Residential home ▪ Billerica ▪ quiet, clean & cozy

Dec 8 – 15

G$33,786 GYD per night

Guest favorite

Guest suite in Salem

4.99 out of 5 average rating, 690 reviews

The Mason Suite of Salem

Mar 25 – Apr 1

G$30,495 GYD per night

Guest favorite

Guest suite in Reading

4.86 out of 5 average rating, 179 reviews

Clean Spacious Suite-Private Entrance-Near Boston

Nov 8 – 15

G$35,509 GYD per night

Guest favorite

Guest suite in Marblehead

4.92 out of 5 average rating, 244 reviews

Ocean Park Retreat

Feb 12 – 19

G$27,756 GYD per night

Guest favorite

Apartment in Wakefield

5.0 out of 5 average rating, 69 reviews

Walk to train, lake and downtown - pets welcome

Nov 13 – 20

G$39,942 GYD per night

Guest favorite

Apartment in Woburn

5.0 out of 5 average rating, 96 reviews

Charming 1 BR private entrance apt commuters dream

Feb 4 – 11

G$25,922 GYD per night

Superhost

Home in Wakefield

4.91 out of 5 average rating, 55 reviews

Beautiful home next to train to Boston, near Salem

Jan 17 – 24

G$55,886 GYD per night

Guest favorite

Apartment in Stoneham

4.99 out of 5 average rating, 91 reviews

Cozy Basement Apartment-Stoneham

Jun 8 – 15

G$22,932 GYD per night

Show all

Quick stats about vacation rentals in Wakefield

Total rentals
30 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.6K reviews
Nightly prices starting at
G$6,269 GYD before taxes and fees

Frequently Asked Questions

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 10 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 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 House Rentals in Wakefield?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Wakefield

Top-rated vacation rentals in Wakefield

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Wakefield vacation rentals

Stay near Wakefield's top sights

Other great vacation rentals in Wakefield

Home in Billerica

Guest suite in Salem

Guest suite in Reading

Guest suite in Marblehead

Apartment in Wakefield

Apartment in Woburn

Home in Wakefield

Apartment in Stoneham

Quick stats about vacation rentals in Wakefield

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there pet-friendly vacation rentals in Wakefield?

Do apartment rentals in Wakefield have wifi?

Do house rentals in Wakefield have air conditioning?

Are there vacation rentals with a dedicated workspace in Wakefield?

How much does it cost to stay in apartment rentals in Wakefield?

What are the most popular amenities for House Rentals in Wakefield?

Destinations to explore