Holiday rentals in Chelsea

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Top-rated holiday rentals in Chelsea

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Home in Revere
5 out of 5 average rating, 9 reviews

Modern 2BR Getaway Near Revere Beach

Experience elevated comfort in this beautifully designed 2-bedroom retreat in Revere, MA. This modern home features curated décor, elegant furnishings, and bright, open living spaces that create a calm, upscale atmosphere. Enjoy plush bedrooms, a stylish dining area, and a cozy lounge perfect for unwinding in comfort. Ideally located near Revere Beach with easy access to Boston & Logan airport, this house blends luxury and convenience for an exceptional stay. Kindly read additional house rules

Top guest favourite
Flat in Beachmont
4.89 out of 5 average rating, 235 reviews

Stunning Oceanview-4 Train Stop Logan Airport

Stunning 1 bedroom huge apartment with partial ocean views of Revere Beach. This upscale home has it all!! Just one flight up then you enter a hardwood floor foyer, opens to a huge living room with upscale decor, large eat in kitchen stainless steel appliance, country table has seating for 4, tile floor, gas range, and lots of cabinet space, with views of Revere Beach and ocean, giant bathroom complete with tiled shower and stackable laundry (Washer and Dryer) and huge bedroom with closet.

Guest favourite
Townhouse in Chelsea
4.82 out of 5 average rating, 566 reviews

10 min Logan Airport- 3Bed/ 2Bath, Sleep 7

Welcome to my charming townhouse in the heart of Chelsea. An ideal retreat for your stay near Boston. Conveniently located just a few miles away from all the Bostons attractions, my townhouse offers easy access to the best that Boston has to offer. Whether you're here for business or pleasure, you'll find everything you need for a memorable stay right at your fingertips. Book your stay at my townhouse today and experience the perfect blend of comfort and convenience for your Boston trip!

Top guest favourite
Townhouse in Everett
4.92 out of 5 average rating, 289 reviews

#9 Modern Home 15 min to Boston w/ Yard & Parking

Stay in this stylish 2-story home with 3 Comfy Bedrooms + 1.5 Baths! Ideal for families or groups, it comfortably fits 6+ guests. Enjoy a fully stocked kitchen, dedicated workspace, and a private backyard with a BBQ & a fire pit. Perfectly located for exploring Boston, Cambridge, and Salem with free private parking. Your memorable stay with experienced Superhosts awaits! 📶 High-Speed Wi-Fi + Smart TVs 🚗 Private Parking for 2 Cars 🧺 In-Unit Laundry 🌆 Easy Access to Local Attractions

Top guest favourite
A cozy seating area includes a gray sofa adorned with a red cushion, situated on an area rug. A tall plant enhances the space, while double doors provide access to additional storage. Soft lighting and neutral walls create an inviting ambiance.
Flat in Everett
5 out of 5 average rating, 32 reviews

Cozy unit near Boston w/parking

Welcome to our cozy and modern Everett retreat the perfect space for couples, solo travelers, or anyone looking for a comfortable stay just minutes from Boston! Located only 5 miles from Downtown Boston and close to public transportation and bus stops, this stylish private suite offers a relaxing atmosphere with everything you need for a convenient and enjoyable stay. Perfect for: ✔️ Couple trips ✔️ Weekend getaways ✔️ Boston visits ✔️ Business travelers ✔️ Airport stays

Superhost
Home in Chelsea
4.83 out of 5 average rating, 416 reviews

10 minutes to Airport-Boston-Casino (2G)

(2G)=Your place is on the 2nd floor and your color code is Green. Do Not include it to the address when you navigate to us. We have a beautiful victorian house built in 1858, owned by our family in 1911, big spaces and high ceilings are a blessing! You can stay here with your family and kids, we have a play room with some toys for fun, a living room, a bedroom and a private full bathroom with a pressure shower. Chelsea is a nice quiet place with a lot to offer.

Top guest favourite
Apartment in Charlestown
4.98 out of 5 average rating, 149 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.

Superhost
A spacious outdoor pool is framed by lounge chairs and shaded by umbrellas. Neat rows of trees and landscaped gardens enhance the inviting atmosphere. The surrounding buildings feature large windows, reflecting the evening sky painted in soft hues.
Flat in Everett
4.94 out of 5 average rating, 104 reviews

Luxury Grand Oasis | Pool · Gym · Parking · 2BR

Discover your exclusive retreat in Everett. Immerse yourself in sleek, curated living with designer finishes and resort‑style amenities for an unforgettable stay. Highlights: • Steps from downtown Boston via easy Silver Line & Route 1 access • Sparkling pool with cabana seating and courtyard fire pits • 24/7 state‑of‑the‑art fitness center & dedicated yoga studio • Private music room, co‑working pods & on‑site community pet spa

Superhost
Flat in Everett
4.67 out of 5 average rating, 9 reviews

Luxurious Open-Concept Home with Roof Skyline View

Enjoy a luxurious stay at this centrally located home, just minutes from the airport, downtown, and Encore Casino. Featuring an open-concept design with high ceilings and stunning views of Everett’s city skyline, this home is perfect for both relaxation and adventure. • Prime Location: Close to key attractions and entertainment. • Modern Comforts: Rooftop deck, Spacious, stylish, and equipped with everything you need.

Superhost
Flat in Chelsea
4.8 out of 5 average rating, 74 reviews

Cozy 1BR Near Boston w/ Pool & Gym

🌟 Features You’ll Love • 1BR w/ king bed • Fast Wi-Fi + workspace • Smart TVs • Full kitchen • Washer/dryer • Private patio • Private parking • Pool, gym, game room & business lounge 📍 Prime Location • Chelsea, minutes from Boston ✨ Perfect For • Business travelers, travel nurses & city stays 💫 Good To Know • Strictly non-smoking Dont miss out- reserve your stay today and enjoy a memorable Boston experience.

Guest favourite
A cozy outdoor space is set in front of a charming brick townhome. A small table and wooden chairs are arranged alongside a grill, with a potted plant on the table. Lush greenery climbs the staircase, which leads to the entrance above.
Guest suite in Admirals Hill
4.97 out of 5 average rating, 179 reviews

Modern Suite Near Boston, Airport & Downtown

Enjoy a spacious, private suite with its own entry and free parking on Admiral's Hill. Nestled in a secure, gated community, this peaceful retreat offers stunning city views and direct access to Mary O'Malley State Park. Perfectly located minutes from Logan Airport. Easy access to downtown Boston via public transit, it’s ideal for both relaxation and convenience.

Top guest favourite
Home in Revere
4.94 out of 5 average rating, 174 reviews

Modern 2-bedroom w/parking near Encore and Logan

Modern two bedroom with free parking, conveniently located 7 minutes from Boston Logan Airport, 5 minutes from Revere Beach and only 12 minutes to Encore Casino and downtown Boston. No parties or events are allowed in the unit. Penalties apply. DISCLAIMER: For your safety and the safety of others, surveillance cameras are installed outdoors at this property.

Popular amenities for Chelsea holiday rentals

When is the best time to visit Chelsea?

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Frequently Asked Questions

  • What are the best places to stay in Chelsea?

    Chelsea has stays in vibrant areas near the waterfront, historic downtown, and residential neighborhoods with parks. Consider places around Broadway and the historic core for unique architecture and access to local shops.

  • What are the best things to do in Chelsea with kids?

    Families frequently suggest visiting Mary O'Malley State Park for playgrounds and harbor views, exploring local libraries for events, or trying hands-on children’s programs at community centers. Seasonal activities and family-friendly eateries are also popular.

  • What are some of the best things to do in Chelsea?

    Explore Mill Creek Riverwalk for waterside strolls, visit the Chelsea Square Historic District for local heritage, or discover neighborhood galleries and murals. Many enjoy relaxing in public parks or discovering local restaurants.

  • How is the weather in Chelsea?

    Chelsea has cold winters around 23–39°F (-5–4°C) and warm summers near 65–82°F (18–28°C), with moderate rainfall throughout the year. Pack layers for cooler evenings and versatile weather, especially in spring and autumn.

  • When is the best time to visit Chelsea?

    Late spring through early autumn is frequently suggested for warmer weather, blooming parks, and outdoor cultural events. Winter has a quieter pace, with festive community events and cozy neighborhood eateries.

  • What are the best places to visit in Chelsea?

    Frequently suggested stops include Mary O'Malley State Park for harbor views, the Chelsea Square Historic District for architectural interest, and local galleries for rotating art exhibits. Walking along the Mill Creek Riverwalk is another popular activity.

  • What are some hiking trails in Chelsea?

    Hikers can explore green spaces like Mary O'Malley State Park for waterside walks, or follow urban trails through neighborhood parks. For a wider variety of trails, wooded paths can be found in public conservation areas around Chelsea.

  • What are some family activities we can do in Chelsea?

    Families can explore local parks like Mary O'Malley State Park, participate in craft and storytime activities at Chelsea Public Library, or enjoy community art projects and sports fields. Many local cafes also welcome children.

  • What are some of the best day trip ideas from Chelsea?

    Many visitors explore Greater Boston’s museums, historic sites, and beaches around the North Shore. Others choose to discover local food markets and coastal parks just outside Chelsea for a change of pace.

  • Are there any pet friendly accommodations available in Chelsea?

    Chelsea has pet-friendly rental options, especially in residential neighborhoods with access to green spaces. Local parks and nearby walking trails make it convenient to travel with dogs.

  • What are some local tips for visiting Chelsea?

    Locals recommend exploring multicultural food options, supporting small shops around Broadway, and checking public art installations. Early mornings are quieter for park strolls, and bringing layers helps with shifting New England weather.

  • What is Chelsea known for?

    Chelsea is known for its vibrant immigrant communities, historic architecture, and rich industrial heritage. Its lively dining scene and public parks contribute to a locally rooted, welcoming atmosphere.

  • What are the best hidden gems to explore in Chelsea?

    Explore local murals and street art throughout Chelsea, walk peaceful paths along Mill Creek, or stop by small bakeries and welcoming community cafes. Neighborhood parks and local art displays invite you to connect with the city's creative spirit.

  • What are the best foods to try in Chelsea?

    Chelsea is known for its diverse mix of Salvadoran pupusas, Vietnamese pho, and traditional New England seafood like fried clams and chowder. Bakeries in the area are often recommended for house-made breads and pastries.

  • What should I bring for a trip to Chelsea?

    Pack comfortable walking shoes for exploring, layers for shifting weather, and a rain jacket for occasional showers. A reusable water bottle and a camera can be helpful for neighborhood strolls and scenic views.

  • What is the nightlife in Chelsea like?

    Chelsea has a low-key nightlife scene with lively neighborhood bars, lounges, and restaurants featuring Latin American and international music. For more nightlife options, visitors often explore nearby Boston neighborhoods.

  • What are the most popular events or festivals in Chelsea?

    Chelsea often hosts community festivals celebrating cultural heritage, arts, and food, especially in the warmer months. Multicultural parades and seasonal celebrations, such as those around summer and autumn holidays, are often community highlights.

  • Are there family friendly vacation rentals in Chelsea?

    Chelsea has vacation rentals in residential neighborhoods that suit families, offering features like extra bedrooms, kitchens, and proximity to parks or playgrounds. Many hosts are happy to welcome children and offer local tips.

Quick stats about holiday rentals in Chelsea

  • Total holiday rentals

    Explore 220 holiday rentals in Chelsea

  • Nightly prices starting at

    Chelsea holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 16,530 verified reviews to help you choose

  • Family-friendly holiday rentals

    100 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 60 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wifi availability

    210 of Chelsea holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chelsea rentals

  • 4.8 Average rating

    Chelsea stays are highly rated by guests – averaging 4.8 out of 5!

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