Best Vacation Homes in Chelsea
1400 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $443/Night
For 7 Nights US $3,104
1399.31 ft²
10 Guests
4 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- View
US $595/Night
For 7 Nights US $4,165
US $178/Night
For 7 Nights US $1,243
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Kitchen
- Parking
US $340/Night
For 7 Nights US $2,378
581.25 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $149/Night
For 7 Nights US $1,043
950 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
US $263/Night
For 7 Nights US $1,838
600 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $227/Night
For 7 Nights US $1,589
550 ft²
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Internet
- Child Friendly
- Security/Safety
US $215/Night
For 7 Nights US $1,504
Chelsea Luxury Rentals
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $696/Night
For 7 Nights US $4,875
1834 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $689/Night
For 7 Nights US $4,824
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Pool
US $559/Night
For 7 Nights US $3,910
5 Guests
2 Bedrooms
2 Bathrooms
Pet Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $555/Night
For 7 Nights US $3,884
1400 ft²
10 Guests
5 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $542/Night
For 7 Nights US $3,791
10 Guests
4 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $497/Night
For 7 Nights US $3,481
882.64 ft²
16 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Parking
- Air Conditioner
- Internet
US $420/Night
For 7 Nights US $2,940
332.15 ft²
1 Bathroom
Ocean View
Hotel
- Private Pool
- Oceanfront
- Fireplace/Heating
US $404/Night
For 7 Nights US $2,829
Chelsea Pet Friendly Vacation Rentals
880 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $337/Night
For 7 Nights US $2,361
1097.92 ft²
5 Guests
1 Bedroom
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $360/Night
For 7 Nights US $2,520
740 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $320/Night
For 7 Nights US $2,240
581.25 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $222/Night
For 7 Nights US $1,554
840 ft²
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $270/Night
For 7 Nights US $1,891
800 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $166/Night
For 7 Nights US $1,163
1200 ft²
7 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $417/Night
For 7 Nights US $2,921
885 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $243/Night
For 7 Nights US $1,699
Chelsea Large Vacation Homes
13993.08 ft²
10 Guests
1 Bedroom
1 Bathroom
Apartment
- Balcony/Terrace
- Air Conditioner
- Internet
US $358/Night
For 7 Nights US $2,506
Why Choose Rent By Owner for your Chelsea Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Chelsea Vacation Rentals
Where are the best neighborhoods to stay in Chelsea?
Exploring neighborhoods in Chelsea, Massachusetts offers a fantastic opportunity to experience a vibrant and diverse community just moments from Boston. Whether you're seeking the lively atmosphere of waterfront areas or quiet residential streets, Chelsea's neighborhoods provide a range of options for your stay. As you consider booking your vacation rental in this charming area, you'll find it easy to access the city’s attractions while enjoying the comfort and convenience of local neighborhoods that cater to various preferences. Discover the best place to stay in Chelsea, where convenient location and authentic neighborhood character come together seamlessly.
Harbor View - Orient Heights
This neighborhood offers stunning views of the harbor, making it an ideal choice for those seeking a peaceful and scenic stay near the water. Here, you can enjoy easy access to waterfront attractions while experiencing the comfort of well-appointed vacation rentals in the region.
View 699+ Rentals in Harbor View - Orient HeightsHarbor View - Orient Heights
Located within close proximity to Boston’s vibrant city life, this area provides a tranquil retreat with convenient transportation options. Your stay here places you near the waterfront and local amenities, perfect for exploring the region's diverse offerings.
View 699+ Rentals in Harbor View - Orient HeightsBest Times to Visit Chelsea
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as this destination offers distinct advantages during different seasons, allowing you to enjoy the region’s unique charm at its best.
Peak Season Highlights
Summer (June to August)
During the warm summer months, you'll enjoy longer daylight hours and vibrant local activity, making it an ideal time to explore the area's outdoor scenery from your vacation rental.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
Fall (September to November)
The fall season offers mild weather and stunning foliage, providing a picturesque setting for your stay in this destination while you take advantage of the region’s cultural events and scenic views.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Winter (December to February)
In the winter, the area experiences cooler temperatures, which can be perfect for cozying up in your vacation rental, away from the crowds, while enjoying the quieter atmosphere.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
Spring (March to May)
Springtime brings milder weather and blooming landscapes, offering a peaceful environment for your visit as nature awakens here, with fewer tourists around for a more relaxed experience.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 40°F to 50°F
Weekly Weather Forecast for Chelsea
How to Book Your Chelsea Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Chelsea
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor seating areas perfect for relaxing and entertaining.
- Benefit from accessible outdoor patios or decks to take in the fresh ocean air.
- Make use of private gardens or landscaped yards that enhance your stay here.
- Utilize convenient outdoor grilling stations for family cookouts with a view.
- Relax on sun loungers or outdoor furniture designed for comfort in the region's mild climate.
- Explore nearby waterfront access points for boating or other water activities.
- Take advantage of scenic views from outdoor balconies or porches overlooking the area.
Top Attractions Around Chelsea
What attractions are nearby?
Nearby, you can explore a variety of outdoor activities and cultural attractions that showcase the vibrant spirit of this destination, making your stay in Chelsea, Massachusetts, a memorable experience.
Family Activities
- Discover the Chelsea Creekwalk Trail: Enjoy a family-friendly outdoor adventure along this scenic trail that offers stunning views of the water and easy access for all ages.
- Visit the Mystic River Park: Spend quality time in this lush park featuring playgrounds, open spaces, and waterfront areas perfect for picnics and relaxed outings with children.
- Explore local maritime history at the Chelsea Historical Society Museum: Engage your family with exhibits that showcase the area's rich maritime past and cultural heritage.
- Take a boat tour from the Chelsea Harbor: Experience the region from a different perspective by hopping on a boat tour that showcases the surrounding waterways and skyline views.
Adult Activities
- Explore the Chelsea Waterfront Park: Stroll along the scenic waterfront offering breathtaking views of Boston Harbor, perfect for relaxing or taking memorable photos.
- Visit the Sargent House Museum: Discover the historical charm and architecture of this renowned museum that highlights the area's rich cultural heritage.
- Experience local dining at Chelsea’s waterfront restaurants: Enjoy fresh seafood and regional cuisine with views overlooking the harbor, ideal for a leisurely meal.
- Walk through the nearby Mystic River Reservation: Engage in outdoor activities like walking or birdwatching within this lush, natural setting just outside the city center.
Other Places to Stay in Chelsea, MA
Naval Hospital Boston Historic District
Apollinaire Theatre Company
Bellingham Square Historic District
Chelsea Garden Cemetery
Mass General: Chelsea HealthCare Center
Boston Paintball
Chelsea Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Eateries: Take advantage of the diverse culinary scene in this destination by trying out popular local restaurants and cafes to truly experience the area's flavors.
- Plan Your Transportation: Utilize nearby public transit options or consider parking strategies to navigate efficiently and make the most of your time here.
- Visit Nearby Attractions: Discover the region’s hidden gems and scenic spots that are easily accessible from your vacation rental for a fuller experience.
- Book Ahead for Popular Experiences: Secure reservations early for sought-after activities or dining venues to ensure seamless enjoyment during your stay here.
Transportation Options
- MBTA Blue Line Subway: This rapid transit option connects you directly to Boston's downtown, making it a convenient way to explore the region from Chelsea.
- Bus Services: Local bus routes provide accessible and affordable transportation around the area and to nearby neighborhoods.
- Taxi and Rideshare Services: Taxis and popular rideshare apps offer flexible, door-to-door travel options within Chelsea and beyond.
- Bike Rentals and Cycling Routes: The area features bike-friendly pathways, allowing you to enjoy scenic rides while exploring Chelsea at your own pace.
Local Customs Options
- Local Seafood Dining Etiquette: When visiting here, you'll notice that sharing fresh seafood dishes is a cherished tradition reflecting the region's maritime heritage.
- Respect for Maritime Heritage: Engaging with local maritime customs, such as participating in boat tour etiquette, helps you connect with this area's rich seafaring history.
- Community Celebrations: Attending neighborhood events often involves customary greetings and participation, which reflect the area's welcoming spirit.
- Historical Preservation Respect: Maintaining reverence for local historical sites means observing guidelines to preserve the region’s cultural landmarks during your stay.
Frequently Asked Questions About Chelsea?
1. What are the top vacation rentals in Chelsea?
There are a lot of options in Chelsea. If you plan on staying in the Chelsea area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chelsea:
- The Maverick Upstairs - Lux Apartment - Near Airport/Downtown - NEW!
- Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
- Modern 2/Bed 2/Bath Condo near Boston # W/Parking
- Cozy/warm Near-Commuter rail, Boston, Airport, Casino and More !
- Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
- The Maverick - Luxurious Apartment - Near Airport/Downtown - Free Parking!
- Hampton Inn Boston Logan Airport Chelsea
- Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea
- Suite at House of L: near Boston, Hospitals, Encore Casino, Walk to Bus, Fast WiFi, Driveway
- The Maverick Downstairs - Lux Apartment - Close to Downtown Boston & Airport
2. Which vacation homes in Chelsea are best for families?
If you are looking for a family-friendly vacation home in Chelsea, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chelsea:
3. How many Rentbyowner vacation rentals are available in Chelsea?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 71 in the Chelsea area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Chelsea.
4. What is the cancellation policy for vacation rentals in Chelsea, Massachusetts?
Cancellation policies vary depending on the individual property. You should review the specific listing details or contact the property owner directly to understand the terms regarding cancellations and any applicable fees.
5. How do I find available vacation rentals in Chelsea, Massachusetts, during my travel dates?
Availability depends on the dates you choose. Use the search filters and calendar on the listing page to see which properties are open for your preferred travel period, or reach out to the host for assistance.
6. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning, service charges, or taxes may apply depending on the listing. Always review the detailed fee breakdown on the property page or contact the owner for clarification before booking.
7. What amenities can I expect from vacation rentals in this area?
Amenities vary by property but often include essentials like Wi-Fi, kitchen facilities, and parking. Check each listing's amenities section for specific features available during your stay.
8. How do I contact the property owner if I have questions about my reservation?
You can message the host directly through the booking platform’s communication system. Owners are generally responsive and happy to assist with any inquiries before or during your stay.
Chelsea Top Rated Vacation Rentals
1 Bathroom
Family Friendly
Hotel
- Pool
- Kitchen
- Parking
US $175/Night
For 7 Nights US $1,223
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
US $185/Night
For 7 Nights US $1,295
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
US $155/Night
For 7 Nights US $1,084
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
US $222/Night
For 7 Nights US $1,556
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
US $200/Night
For 7 Nights US $1,400
365.98 ft²
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $251/Night
For 7 Nights US $1,757
443.47 ft²
3 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $247/Night
For 7 Nights US $1,726
287.04 ft²
3 Bathrooms
Ocean View
Hotel
- Private Pool
- Oceanfront
- Fireplace/Heating
US $256/Night
For 7 Nights US $1,789
