
Holiday rentals in Wakefield
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Top-rated holiday rentals in Wakefield
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Luxury Oceanview Suite in Victorian on Independence Park
Bask in beautiful sunrises and peaceful ocean sounds from a generous seaside room with wet bar. The 42” Art Frame TV offers Xfinity, Netflix, and Hulu Plus apps, while the space itself has large windows and a bright, sophisticated interior and is only steps from the beach. Terrific ocean views from this newly renovated suite. Easy access to the beach, paddle board rentals on the weekend right outside your door, walking to Dane Beach, a quick walk to Cabot Street and the cafe's and restaurants nearby. A well equipped wet-bar with fridge, freezer, microwave, coffee maker and tea set ups, and a newly renovated bathroom with heated floors and double shower complete the space. A 42” Art Frame TV with the Xfinity, Netflix and Hulu Plus apps. Enjoy your favorite shows or leave the TV in art mode. We are available by phone or text always but we live just a few houses away, so we can be reached almost anytime. We generally leave guests alone and respect your privacy but can be available if necessary. On the North Shore of Massachusetts, about 26 miles from Boston, Beverly has small-town charm coupled with a city identity. Located close to vibrant Cabot Street in downtown, there are recreation, shopping, and dining options for all tastes. Beverly has excellent access to Route 128 and five commuter rail stations. The house is just a 10-15 minute walk to the Beverly Depot (first Beverly stop on the MBTA commuter rail). It's a bout a 20 minute ride to North Station in Boston.

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.

#7 Spacious Modern Home Near Boston w/ Parking
Discover comfort & convenience minutes from Boston, Cambridge, & Salem. Whether you're here for work, family, or fun, this stylish 2-story home has everything you need for a relaxing & memorable stay, plus we are experienced Superhosts! 🛏 3 Comfy Bedrooms + 1.5 Baths 🍳 Fully Equipped Kitchen 📶 High-Speed Wi-Fi + Smart TVs 🚗 Private Parking for 2 Cars 🧺 In-Unit Laundry 🔥 Backyard BBQ + Fire Pit + Outdoor Seating for 6 🌆 Easy Access to Local Attractions 🏡 Perfect for families 5⭐ 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.

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!

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!

Entire Apartment in Stoneham
Welcome to our cozy, beautiful, and well-equipped home—your perfect retreat in the heart of Stoneham. Wake up in this bright and inviting apartment, just 20 minutes from the airport and the historic city of Boston. You’ll be conveniently close to shopping malls, restaurants, coffee shops, grocery stores, and the stunning nature of Middlesex Fells Reservation and Stone Zoo. Whether you’re here to explore or unwind, this charming home will make your trip both enjoyable and stress-free.

Quaint Little New Hampshire Lake House Getaway!
Imagine the peace and quiet of looking out a wall of glass seeing the tranquility of the lake while knowing 10 minutes away is shopping, restaurants entertainment and just about anything you could ask for to meet your needs. 10 minutes from the highway, 35 minutes from Boston, 35 minutes from the ocean and 1 1/2 hours from the mountains. We are a central point to anything you’re looking for. Newly renovated lake house with all the up to date amenities. Come and enjoy a night or week.

Large 1+bed in historic Charlestown, Boston!
Large 1 BR condo. This is a brick 3 story home & the rental condo is on the 1st floor only. Luxurious KING sized bed, work desk area, living room w/queen pull out bed, fully equipped kitchen & private deck/courtyard. Washer/dryer. Convenient walk to cafes & restaurants, Whole Foods, MBTA, Freedom Trail, Bunker Hill Monument, USS Constitution. Courtyard is broken down Dec-March & NO smoking in house and NO smoking in courtyard. Not suitable for children under 6 years old.

Winery Farmhouse w/ Private Hot Tub & Wine Tasting
Vineyard Retreat — Experience the elegance and sophistication of the newly remodeled Ice House, a luxurious farmhouse offering breathtaking vineyard views and abundant natural light. Part of the historic Marble Ridge Farm established in 1680. Your stay includes a complimentary wine tasting and 10% off all wine purchases,. Located just minutes from top-rated restaurants, shopping, and highways, it's a destination to relax, rejuvenate, and create unforgettable memories.

Modern Victorian close to Salem
Welcome to The Ulman! Enjoy a stylish experience in our centrally-located historic condo. We are walkable to exquisite beaches and parks as well as downtown Swampscott where you will find shops, restaurants & bars to explore. If you feel like hanging in, share a meal in our well stocked kitchen or a cocktail in the parlor. Perfect for a couples getaway, small family or a group of friends looking to explore the North Shore.

Your Cozy 1 BR Apt & Relaxing Retreat
Romantic Luxury Getaway • Private Jacuzzi • Fire Pit • BBQ • Near Boston Escape to this cozy 1-bed retreat made for relaxation and special moments. Enjoy your private jacuzzi, unwind by the fire pit, and grill on the BBQ for the perfect night in. Located in a quiet area just minutes from Boston, restaurants, and shopping — the ideal spot for couples or a peaceful weekend escape.
Popular amenities for Wakefield holiday rentals
Stay near Wakefield's top sights
Other great holiday rentals in Wakefield

Newly renovated Boston Condo

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Rare, Private 2-Bed near Historic Wayside Inn!

Charlestown Furnished 1 bedroom Apartment M465

The Grand Residence

Quiet 2BD Single-Family, Parking, No Shared Walls!

Winchester Apartment on Greenway

Charming Waterfront Cottage Near Cambridge/Boston
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- Hampton Beach
- Fenway Park
- TD Garden
- Harvard University
- Boston Common
- Revere Beach
- Brown University
- Boston Seaport
- Boston University
- Freedom Trail
- New England Aquarium
- MIT Museum
- Boston Convention and Exhibition Center
- Gillette Stadium
- Canobie Lake Park
- Crane Beach
- York Harbor Beach
- Quincy Market
- Duxbury Beach
- Museum of Fine Arts
- North Hampton Beach
- Prudential Center
- Roxbury Crossing Station
- Boston Children's Museum




