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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Top guest favourite
Townhouse in Somerville
4.96 out of 5 average rating, 157 reviews

Modern Somerville Cottage

My place is a beautiful new house located in the Hip neighborhood of Davis Sq in Somerville. Conveniently on the bike bath leading to Davis Sq with its T stop and all its great restaurants and bars (15 min walk). 2 Mins walk to the new Green line extension that takes you to Cambridge and Boston. Modern furnishings throughout with amazing light from all sides and double height cathedral ceilings in the living/dinning room. I also have 2 beautiful condos in Killington VT please ask for info

Top guest favourite
A spacious living area with a plush sectional couch in a neutral tone, centered around a coffee table, invites relaxation. Large sliding glass doors frame panoramic ocean views and provide natural light. A modern gas fireplace and stylish decor enhance the cozy atmosphere.
Flat in Beachmont
4.97 out of 5 average rating, 174 reviews

Beachmont Guest Suite

Experience tranquility in our modern guest suite with stunning ocean views and a private deck overlooking the Atlantic. Wake up to breathtaking sunrises and relax by the cozy gas fireplace. Features a fully equipped kitchen with island seating, a comfortable queen bed, a plush sectional couch, and a luxurious bathroom. Just minutes from Boston, enjoy beachfront living—ideal for romantic getaways, peaceful retreats, or business travelers. Book now to experience the best of beachfront living!

Guest favourite
A light gray living space features a comfortable sofa adorned with decorative pillows. A round coffee table sits in the center, complemented by a soft area rug. Two windows, including a skylight, provide natural light and views of the exterior.
Flat in Everett
4.87 out of 5 average rating, 301 reviews

Huge 1BR w/King Bed near Airport, Boston, Salem

Location: Quick 10-20 mins to the center of Boston, 25 mins to Salem. Easy access via multiple major highways, or walk 0.7mi (HILL) to bus, taking you directly into the city. This unit is an upper-level apartment of our home (i.e., STAIRS). Enjoy self-check-in and a reserved parking spot. Living room: Roku enabled TV. Mini-kitchen: Two burner stovetop, microwave, a 4 cu. sqft fridge, and a Keurig. Bedroom: king-sized bed with down alternative pillows and tempur-pedic memory foam topper.

Guest favourite
A wooden table featuring a natural, textured surface holds a decorative bowl and a small green plant. A softly lit lamp and a vase with white flowers are also visible. The wall art depicts two silhouettes of deer amid foliage, adding a serene touch.
Guest suite in Revere
4.86 out of 5 average rating, 111 reviews

Studio Close to Beach, Boston, Airport & Train

Modern and cozy basement studio just 10 minutes drive from Logan Airport, 5 minutes from Revere Beach, and 14 minutes from Downtown Boston. Fully equipped with a kitchenette, full bathroom, high-speed internet, and a 75-inch Smart TV. Enjoy entertainment options like a foosball table, Xbox, and board games. Step outside to a private lounge area with a fireplace and grill. Free driveway parking and plenty of nearby restaurants make this the perfect home base for comfort, convenience, and fun.

Superhost
A wooden tray is displayed on a light-colored table, featuring a bottle of white wine and two clear wine glasses. A small potted orchid adds a touch of elegance, complemented by a simple mirror in the background.
Flat in Chelsea
4.82 out of 5 average rating, 467 reviews

10 min Logan Airport- 2 Bed/2 Bath, Sleep 5

Welcome to our 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, our 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 our townhouse today and experience the perfect blend of comfort and convenience for your Boston trip!

Top guest favourite
A stone sign marked 'BEACHMONT' stands prominently at the entrance of a landscaped area. Surrounding features include a stone-paved pathway, a bench, and several tables. Lush greenery lines the background, providing a natural backdrop to the welcoming space.
Home in East Boston
4.78 out of 5 average rating, 223 reviews

Renovated Cozy City Getaway

Newly renovated cozy 1 bedroom home located on the hills of Beachmont, walking distance from the MBTA train station and Revere Beach. Enjoy sitting on the deck overlooking the Belle Isle Marsh Reservation and Boston Logan Airport in the distance. Take a walk along the beach or take the train into Boston. The location is a 5-10 minute ride to the Airport and a 15 minute train ride to downtown Boston. The unit has new furnishings (2021), modern appliances, and is beautifully decorated.

Guest favourite
A bright studio space features a spacious bed with a light-colored blanket. Decorative wall art hangs above the bed, while a cozy seating area with a gray sofa and a coffee table is visible in the background. Natural light streams through nearby windows.
Flat in Revere
4.92 out of 5 average rating, 197 reviews

Corner Cottage - cozy studio just north of Boston

Whether you’re a tourist visiting Boston for the weekend, a traveling nurse in search of a medium-term stay, or a pilot/flight attendant needing overnight accommodations, this completely renovated and professionally cleaned AirBnB is perfect for you! Finding living accommodations is tough; finding a reliable and responsive host is even tougher. Not only is this unit well equipped with almost everything you may need, but I will do my best to ensure your stay is the most comfortable.

Guest favourite
A modern living area features a comfortable sectional sofa and a wooden coffee table on a soft area rug. Natural light enters through large windows, illuminating a television on a stand and a pair of lamps on a sideboard.
Flat in Chelsea
4.96 out of 5 average rating, 25 reviews

Spacious 2 bedroom apartment.

Spacious and modern 2-bedroom, 2-bathroom apartment in Chelsea, MA—just a short ride from downtown Boston! This beautifully furnished space is perfect for both business and leisure travelers. Enjoy a wide range of luxury amenities including a resort-style pool, fully equipped gym, basketball court, resident lounge, outdoor patio, and a pickleball court. Free onsite parking and nearby public transportation make getting around a breeze. Relax, work, and play in comfort and style!

Guest favourite
The spacious bedroom features a king-sized bed with a dark quilt and layered patterned bedding. Soft lamps provide ambient lighting on either side of the bed, which is set against a wall adorned with dark curtains. A flat-screen TV is positioned across from the bed, with an air conditioning unit nearby.
Guest suite in Melrose
4.92 out of 5 average rating, 568 reviews

Private Suite-Free Parking,near Boston Airp-Train

--> 7 miles N of Boston & a near subway, beaches, & airport (93, 95 & Rte 1), you’ll find the quaint city of Melrose. During 11/25 - 3/26 longer stay are possible. Please inquire. The Melrosian Suite is nestled behind other houses. Wake up to the chirping birds instead of Boston’s noise. 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.

Guest favourite
A spacious bedroom is shown, featuring a black bed with a textured bedding set displaying ocean waves. A cozy armchair sits beside a radiator, and a small folding table is placed nearby. Natural light enters through a window with patterned curtains.
Home in Chelsea
4.83 out of 5 average rating, 406 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
An inviting living area features a grey recliner and a brown sofa, arranged on an orange and grey patterned rug. A large TV is mounted on the wall, while a dining table is visible in the background surrounded by chairs. Natural light filters through the windows.
Flat in Medford
4.99 out of 5 average rating, 157 reviews

Couples Retreat - Apt in Charming Colonial Home

Newly renovated, open concept apartment in a private home located on a quiet residential street. Single, queen-sized adjustable bed, steam shower, and oversized bubble jet tub make this an ideal retreat for stress free relaxation. Includes off-street parking, full-size washer and dryer, and the use of both front and rear porches with seating in season. This apartment is great for couples or individuals looking to relax and get a break from their busy lives.

Top guest favourite
A living room is featured with hardwood floors and exposed brick walls, creating a cozy ambiance. A large TV sits atop a white media console. A comfortable blue chair with a patterned cushion provides seating, while a coffee table enhances the space. Artwork decorates the walls.
Flat in Chelsea
4.94 out of 5 average rating, 413 reviews

5 minutes to downtown. Charming. Clean. Cozy.

THE CHELSEA HOUSE: A well-maintained 1900s apartment located on the third floor of a quiet, clean three-family brick building on a small one-way street. It features hardwood floors, exposed brick, and slanted loft ceilings creating a charming, warm, and cozy atmosphere. Parking is included. The Chelsea House is our home away from home, and we have decided to share it with others. Thank you in advance!

Popular amenities for Chelsea holiday rentals

When is the best time to visit Chelsea?

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Avg. price$145 SGD$148 SGD$151 SGD$170 SGD$183 SGD$182 SGD$192 SGD$176 SGD$183 SGD$193 SGD$169 SGD$154 SGD
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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 $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 16,710 verified reviews to help you choose

  • Family-friendly holiday rentals

    90 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

    100 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

  • 4.7 Average rating

    Chelsea stays receive an average rating of 4.7 out of 5 from guests

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