Condo vacation rentals in Chelsea

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Top-rated condo rentals in Chelsea

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Top guest favorite
The exterior of a historic two-story building is shown, featuring blue siding and white trim. A tall tree stands at the front, providing shade, while a decorative fence encloses the property. Steps lead up to the entrance, enhancing the welcoming appeal of the home.
Condo in Winthrop
4.98 out of 5 average rating, 106 reviews

The Day-Burrill-Wadsworth-La Voix House

The Day-Burrill-Wadsworth-La Voix House is located in Winthrop, MA in the North Shore of Boston. Super close to Logan Airport for your traveling needs. A Level 2 EV Charger is available! This renovated 3 Bedroom penthouse apartment features a private roof deck, off-street parking, sunroom, and free in-unit laundry! A safe, spacious, and serene space. A historic building, it was one of the first handful of homes in Winthrop... built in 1860 (but since converted to two apartments and renovated).

Superhost
A spacious living area features a dark sectional sofa adorned with decorative pillows in varying colors. A glass coffee table is positioned in front, while a baby grand piano is visible in the background, alongside large windows that allow natural light to fill the space.
Condo in Medford
4.81 out of 5 average rating, 151 reviews

Peaceful/Sunny Apt w/Baby Grand Piano Near Transit

Pristine clean interior. WIFI/Cable TV, AC in all rooms. Fully Equipped Kitchen, a Baby Grand Piano., share Washer & Dryer. Safe to walk 24/7. Near Mystic River, 6 min driving from downtown Boston, Harvard & Tufts Univ, Fenway Park, TD Garden, Casino, all major Hospitals. Walk to Subway Station, supermarket, 24/7 pharmacy. Private parking ($15 per day) or free Street parking one block away. Near Mystic River reservation, ideal for hiking, biking. Short access to all highways, leading to Salem

Guest favorite
An open-concept living area showcases a modern kitchen with white cabinets and stainless steel appliances. A dining table is positioned adjacent, with seating for four. Comfortable seating is provided by a light-colored sofa and stylish chairs, complemented by a textured area rug.
Condo in East Boston
4.95 out of 5 average rating, 133 reviews

Modern Luxury | Free Parking, Near T | Home Cinema

Welcome to our stylish East Boston condo! Just a 5-minute walk to the Blue Line and 11-minute drive (or 25-min walk) to Logan Airport. Only two blocks from the waterfront with stunning Boston skyline views. This modern farmhouse retreat features two cozy bedrooms plus two more beds downstairs. The sleek kitchen and dining area are great for meals or morning coffee. Relax in the comfy living room or enjoy movie nights on the 135-inch home theater. Includes in-unit laundry and off-street parking.

Top guest favorite
Condo in Winthrop
4.99 out of 5 average rating, 224 reviews

Truly Oceanfront! Spacious Family Petfriendly Home

Truly ocean-front! Don’t be fooled by Winthrop listings of side-street homes. This is an entire 1st floor unit with a private entrance. In an owner-hosted, classic triple-decker home with normal family/town sounds. Pro-cleaned and pet-friendly. Adjacent to Boston by car, ferry/transit. Family time with everything you need. Enjoy our rocky beach or walk a few blocks north to the sandy, lifeguarded stretch. Cafés and restaurants are walkable, and groceries deliver. Quiet hrs: 10pm-7am for all.

Superhost
A comfortable outdoor seating area is presented on a covered porch. The space features a sectional sofa and four wicker chairs arranged around a glass coffee table. Views of nearby buildings and a clear blue sky can be seen in the background, enhancing the serene environment.
Condo in Somerville
4.83 out of 5 average rating, 252 reviews

Spacious, cozy home near Boston!

Stylish, spacious home 15 minutes from the heart of Boston including downtown Boston, Back Bay, Beacon Hill. Minutes away from MBTA green line (Sullivan) and orange line (Assembly). Assembly Square full of restaurants, bars and shops 5 minutes away! Short drive to Harvard/Tufts/Northeastern/BU and other major universities. - NEWLY renovated home - Brand new furniture - 3 bedrooms, 3 bathroom - Fully equipped kitchen - Fully equipped bathrooms with towels and toiletries - Professional clean

Top guest favorite
The modern kitchen features sleek stainless steel appliances and a spacious island with seating. Natural light fills the area from multiple windows, highlighting the granite countertops. A dining table sits within the open layout, creating an inviting space for meals.
Condo in Medford
4.96 out of 5 average rating, 100 reviews

Modern, Spacious, Top Floor Condo in A++ Location!

Modern, sunny second floor space with chef's kitchen! Newly renovated with gleaming hardwood floors, ample free parking, in-suite laundry, seventy five inch 4K smart TV, dining area, two generous bedrooms (one has king bed), separate living room, and sun porch. All this located in an exceptional location just steps from the Wellington Station Orange Line MBTA (the T) / Station Landing, Starbucks, Encore Boston, Life Time Sports Club, Planet Fitness, Restaurants, CVS, Assembly Row, & morer

Top guest favorite
A raven figurine stands atop a vintage-style book, with a lightbulb suspended above it. The background features an intricate dark floral pattern, adding to the gothic ambiance of the setting.
Condo in Salem
4.95 out of 5 average rating, 105 reviews

The Raven!

Looking for the quintessential Salem stay? Look no further! The main bedroom is designed to get you in the Salem spirit, with its dark gothic decor. Take a reading break in the adjacent room, outfitted to look like a Victorian British library. A spacious living room, dining room, kitchen, and full bath complete this lovely property. Enjoy parking in a driveway in the typically-packed city. We are just a quick and enjoyable 12-minute walk to Essex street and all that downtown has to offer!

Top guest favorite
A modern living area features a black leather sofa paired with decorative pillows. A white area rug lies beneath a coffee table, complemented by an accent chair with a geometric pattern. Natural light filters through the two windows, creating a bright and inviting space.
Condo in Cambridge
4.92 out of 5 average rating, 866 reviews

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee

A brand new spacious 3rd floor apartment over 1,000 sq ft centrally locate, near 2 subway stations/bus line, 4 grocery stores within 10 mins walk. The apt has a big kitchen, roof top deck and a huge yard. All brand new furnitures from Crate & Barrel, Pottery Barn and West Elm. Bed sheet sets from Crate & Barrel. NO Cleaning fee. We offer a great atmosphere, high quality amenities and cleanliness are utmost importance. Please read the reviews from prior guests.

Top guest favorite
An open kitchen is paired with a comfortable living area, featuring light hardwood floors. The kitchen includes modern appliances and a spacious island with seating. A neutral-colored sofa and coffee table create a relaxed ambiance, with plants adding a touch of greenery in the background.
Condo in Boston
4.95 out of 5 average rating, 301 reviews

3-Bedroom Apt (7W2) 20-Minuite To Downtown Boston

Perfect for families and groups, this clean, newly renovated 3-level home has 1 King and 2 full size bedrooms and sofa sleeper in living room 2.5 bathrooms (including a half bath on the main floor), and thoughtful touches like snacks, coffee, wine, chargers, travel crib, and fast Wi-Fi. Located in an authentic Boston neighborhood ~20–30 min from downtown by car or transit. Expect lively local character, easy access to public transport, and normal city sounds.

Top guest favorite
A living area displays a light-colored sofa adorned with patterned pillows, accompanied by two blue armchairs. A sleek work desk and a television are positioned near an elegant marble fireplace. Natural light fills the room, highlighting the wooden flooring and soft color palette.
Condo in Charlestown
4.98 out of 5 average rating, 147 reviews

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. KING 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.

Top guest favorite
The living room features a dark sofa with teal accent pillows, complemented by a wooden coffee table. A light fixture hangs from the ceiling, and natural light fills the space through large windows. A small dining table with two chairs is visible, enhancing the cozy layout.
Condo in Beacon Hill
4.97 out of 5 average rating, 357 reviews

Gorgeous Beacon Hill 1BR | 1BA

Come stay at our lovely condo in the heart of Boston's most desirable neighborhood, Beacon Hill! Our newly renovated 1 bedroom | 1 bathroom condo comfortably sleeps three adults and comes with everything you need for an enjoyable stay. Whether you want to walk the Freedom Trail, visit a relative at Mass General, or shop on Newbury St, you will find it all within walking distance. You could not be more centrally located to take in all the city has to offer.

Top guest favorite
The living area features two gray sofas positioned around a round wooden coffee table on a vibrant blue area rug. A cozy fireplace is situated against a striking red wall, complemented by a bookshelf filled with books. Natural light enters through a nearby window.
Condo in East Boston
4.93 out of 5 average rating, 242 reviews

Family Home + Near Downtown + Cool Backyard!

Welcome to our family home. It's convenient, comfortable, safe, and close to downtown Boston! We have a backyard and open space with a beautiful deck. It's a great place to spend time and enjoy a peaceful outdoor setting in the city. Located in the waterfront neighborhood of Jeffries Point, East Boston. A 5-minute walk to lovely parks and the HarborWalk. And just ONE SUBWAY STOP to downtown Boston. We love Boston - and hope we can share it with you!

Popular amenities for Chelsea condo rentals

When is the best time to visit Chelsea?

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Quick stats about condo rentals in Chelsea

  • Total vacation rentals

    Explore 10 vacation rentals in Chelsea

  • Nightly prices starting at

    Chelsea vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

  • Verified guest reviews

    Over 850 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Chelsea vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chelsea rentals

  • 4.6 Average rating

    Chelsea stays receive an average rating of 4.6 out of 5 from guests

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