Chestnut Hill holiday rentals
We found 2,437 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Chestnut Hill that are perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll have the amenities that you expect and more, including parking and a TV. You're sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts – Chestnut Hill
Showing deals for:25 Dec - 1 Jan

Exceptional
(96 reviews)
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Boston
AU$16,759
for 7 nights, 1 home
AU$2,394 per night
includes taxes & fees

Exceptional
(6 reviews)
Luxury Tuscan style villa just few miles from downtown Boston .Newton Reg #24-17
Newton
AU$25,207
for 7 nights, 1 home
AU$3,601 per night
includes taxes & fees

Exceptional
(14 reviews)
Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station
Boston
AU$7,891
for 7 nights, 1 home
AU$1,127 per night
includes taxes & fees

Exceptional
(21 reviews)
Charming 2-bedroom house with a hidden garden in lovely Cambridge.
Cambridge
AU$4,691
for 7 nights, 1 home
AU$670 per night
includes taxes & fees

Exceptional
(21 reviews)
Modern home-like 3BR2BA Retreat/Minutes to T
Boston
AU$5,875
for 7 nights, 1 home
AU$839 per night
includes taxes & fees

Wonderful
(19 reviews)
Newly Renovated Modern Retreat l Near T
Boston
AU$5,785
for 7 nights, 1 apartment
AU$826 per night
includes taxes & fees

Wonderful
(24 reviews)
Brand-new Modern 4BR Boston Comfortable Apartment w/Parking Pet-Friendly - 80/2
Boston
AU$5,648
for 7 nights, 1 apartment
AU$807 per night
includes taxes & fees

Exceptional
(69 reviews)
2 bedrooms with air-conditioning, parking, laundry, WiFi near Sam Adams & subway
Boston
AU$3,502
for 7 nights, 1 apartment
AU$500 per night
includes taxes & fees

Exceptional
(12 reviews)
4BR Near Downtown Boston Private Driveway Parking & 1-Min Walk to Train
Boston
AU$7,390
for 7 nights, 1 apartment
AU$1,056 per night
includes taxes & fees

Very good
(6 reviews)
6BR3BA w Parking Near T I Foosball & Family Space
Boston
AU$6,958
for 7 nights, 1 apartment
AU$994 per night
includes taxes & fees

Exceptional
(44 reviews)
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Boston
AU$7,636
for 7 nights, 1 apartment
AU$1,091 per night
includes taxes & fees

Exceptional
(8 reviews)
3-bedroom 2 baths beautiful victorian with WiFi, AC
Boston
AU$6,465
for 7 nights, 1 apartment
AU$924 per night
includes taxes & fees

Exceptional
(78 reviews)
The Pistachio Room at TPH - Boston
Boston
AU$1,397
for 7 nights, 1 room
AU$200 per night
includes taxes & fees

Exceptional
(11 reviews)
Comfy, Stylish Apt. Near Uni's, Driveway
Somerville
AU$5,150
for 7 nights, 1 apartment
AU$736 per night
includes taxes & fees

Exceptional
(45 reviews)
A Cozy 5BR Apartment near Harvard Square and MIT
Cambridge
AU$5,623
for 7 nights, 1 apartment
AU$803 per night
includes taxes & fees

Exceptional
(52 reviews)
A beautiful 3BR Apartment near Harvard and MIT.
Cambridge
AU$4,152
for 7 nights, 1 apartment
AU$593 per night
includes taxes & fees

Very good
(10 reviews)
3-bedroom apartment in charming Boston/ Near Train
Boston
AU$5,024
for 7 nights, 1 apartment
AU$718 per night
includes taxes & fees

Exceptional
(24 reviews)
Cozy Cambridge 2bed 2bath w/ Patio & Parking Pass
Cambridge
AU$4,400
for 7 nights, 1 home
AU$629 per night
includes taxes & fees

Exceptional
(28 reviews)
3BR2BA Retreat - 2min to Savin Hill Station
Boston
AU$5,576
for 7 nights, 1 apartment
AU$797 per night
includes taxes & fees

Exceptional
(89 reviews)
Special! One of VRBO's Most Popular!! L@@K 1.5 miles to center of Attractions!
Boston
AU$2,288
for 7 nights, 1 apartment
AU$327 per night
includes taxes & fees

Wonderful
(15 reviews)
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
Winthrop
AU$1,955
for 7 nights, 1 apartment
AU$279 per night
includes taxes & fees

Exceptional
(83 reviews)
Special!!excellent, Sunny! Duplex!! Pvt! Condo! 1.5 Miles to Center
Boston
AU$2,288
for 7 nights, 1 apartment
AU$327 per night
includes taxes & fees

Wonderful
(6 reviews)
Fort Hill Inn-- 2 bedroom Duplex, With a touch of modernity! Minutes to Center
Boston
AU$3,791
for 7 nights, 1 apartment
AU$542 per night
includes taxes & fees

Wonderful
(34 reviews)
Fort Hill Inn, Boston *Sunny* 2 bed Duplex, Spacious! ! Minutes to Center!!
Boston
AU$3,755
for 7 nights, 1 apartment
AU$536 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Chestnut Hill
Find the best place to stay - Chestnut Hill

Modern 5BR 3BA • Retreat Near Subway & Downtown • Free Parking
Sleeps 16 · 5 bedrooms · 3 bathrooms

Perfect for large group 10 beds• 4.6 mi to Downtown •steps to T 5BD/2Bth
Sleeps 18 · 5 bedrooms · 2 bathrooms

NEW! Boston Full Home Near MBTA! 3 Mi To Fenway!
Sleeps 16 · 8 bedrooms · 3 bathrooms

Private Base, #Boston medical #Boston Collage, #The Country Club T+Prk
Sleeps 6 · 3 bedrooms · 1 bathroom

FIFA World Cup Stay! Luxury 6,000 Sq Ft Home Near Boston
Sleeps 9 · 6 bedrooms · 4+ bathrooms

Adams Village 6-Bed Apt: City Perks, Suburban Vibe
Sleeps 16 · 6 bedrooms · 2 bathrooms
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the best area to stay in Chestnut Hill when booking a holiday rental?
When considering a holiday rental in Chestnut Hill, Massachusetts, one of the most appealing areas to stay in is the neighbourhood surrounding the Chestnut Hill Reservoir. This picturesque area offers a unique blend of suburban charm and urban convenience. The reservoir itself is a lovely spot for a leisurely stroll or a picnic, providing scenic views and a peaceful atmosphere.Another attractive neighbourhood is the area near the Chestnut Hill Shopping Centre, which features a variety of shops and dining options. This location is particularly convenient for those looking to enjoy a bit of retail therapy or a delightful meal without venturing far from home.In terms of properties, Chestnut Hill boasts a range of accommodations that cater to different needs and budgets, with many charming homes available for holiday rentals.
When is the best time to visit Chestnut Hill for a holiday rental?
April is the most popular month to visit Chestnut Hill, as it falls within the peak season from March to May. This springtime period is great for those looking to enjoy the blossoming beauty of the area, with mild temperatures ranging from 5 to 15 degrees Celsius. Visitors can relish in outdoor activities such as strolling through scenic parks, exploring charming neighbourhoods, and experiencing the vibrant local culture.During April, Chestnut Hill showcases its stunning landscapes, particularly with the blooming of cherry blossoms and other spring flowers, which make for picturesque walks and delightful sightseeing opportunities. The pleasant climate encourages visitors to spend time outdoors, whether it's enjoying a leisurely picnic or exploring the historic sites nearby.For those who prefer a quieter experience and are seeking good value, consider visiting in October. This month offers a serene atmosphere where you can witness the stunning autumn foliage, making it an excellent choice for scenic drives and peaceful exploration.
What are the top attractions in Chestnut Hill?
In Chestnut Hill, Massachusetts, visitors can enjoy a mix of cultural and natural attractions. The renowned Chestnut Hill Reservoir offers scenic walking paths and beautiful views, making it a great spot for outdoor enthusiasts. Nearby, the Boston College campus showcases stunning architecture and is home to the McMullen Museum of Art, which features a diverse collection of contemporary and classical works.For those interested in shopping and dining, The Street Chestnut Hill is a vibrant open-air lifestyle centre with a variety of shops and restaurants, great for an afternoon out.
Are all fees included in the Chestnut Hill holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Chestnut Hill holiday homes with parking?
Stayz offers a wide selection of holiday homes in Chestnut Hill with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Chestnut Hill holiday homes?
You can find great discounts on holiday homes in Chestnut Hill on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Chestnut Hill holiday home booking on Stayz?
To find Chestnut Hill holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Chestnut Hill?
A long-stay holiday home in Chestnut Hill is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Chestnut Hill holiday home?
Book your Chestnut Hill holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chestnut Hill?
Prices for holiday homes in Chestnut Hill vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Chestnut Hill to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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