Chestnut Hill holiday rentals
We found 2,551 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:6 Nov - 13 Nov
Exceptional
(6 reviews)
Luxury Tuscan style villa just few miles from downtown Boston .Newton Reg #24-17
Newton
AU$25,800
for 7 nights, 1 home
AU$3,686 per night
includes taxes & fees
Exceptional
(28 reviews)
Funky and cozy home ! A little bit of everything for everyone.
Arlington
AU$5,417
for 7 nights, 1 home
AU$774 per night
includes taxes & fees
Exceptional
(19 reviews)
Charming 2-bedroom house with a hidden garden in lovely Cambridge.
Cambridge
AU$4,800
for 7 nights, 1 home
AU$686 per night
includes taxes & fees
Exceptional
(20 reviews)
Modern home-like 3BR2BA Retreat/Minutes to T
Boston
AU$6,012
for 7 nights, 1 home
AU$859 per night
includes taxes & fees
Very good
(6 reviews)
6BR3BA w Parking Near T I Foosball & Family Space
Boston
AU$7,119
for 7 nights, 1 apartment
AU$1,017 per night
includes taxes & fees
Exceptional
(36 reviews)
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Boston
AU$7,812
for 7 nights, 1 apartment
AU$1,116 per night
includes taxes & fees
Wonderful
(7 reviews)
Relaxing 2-BR townhome steps to MIT, Harvard, T Red Line, food & more!
Cambridge
AU$4,221
for 7 nights, 1 home
AU$603 per night
includes taxes & fees
Exceptional
(6 reviews)
3-bedroom 2 baths beautiful victorian with WiFi, AC
Boston
AU$6,615
for 7 nights, 1 apartment
AU$945 per night
includes taxes & fees
Exceptional
(48 reviews)
World Cup 4BR Near Downtown Boston Parking & 1-Min Walk to Train
Boston
AU$6,068
for 7 nights, 1 apartment
AU$867 per night
includes taxes & fees
Wonderful
(18 reviews)
Newly Renovated Modern Retreat l Near T
Boston
AU$5,919
for 7 nights, 1 apartment
AU$846 per night
includes taxes & fees
Exceptional
(12 reviews)
4BR Near Downtown Boston Private Driveway Parking & 1-Min Walk to Train
Boston
AU$6,490
for 7 nights, 1 apartment
AU$927 per night
includes taxes & fees
Exceptional
(46 reviews)
Fort Hill Inn- Modern City Triplex !**L@@K **Minutes to Center! With Parking!
Boston
AU$6,995
for 7 nights, 1 apartment
AU$999 per night
includes taxes & fees
Exceptional
(25 reviews)
3BR2BA Retreat - 2min to Savin Hill Station
Boston
AU$5,706
for 7 nights, 1 apartment
AU$815 per night
includes taxes & fees
Exceptional
(110 reviews)
Charlestown Houseboat Walk to attractions Be rocked to sleep
Boston
AU$2,688
for 7 nights, 1 houseboat
AU$384 per night
includes taxes & fees
Exceptional
(37 reviews)
**Fresh** Modern Triplex in a Classic Boston Row House, Amazing City Views!
Boston
AU$7,023
for 7 nights, 1 apartment
AU$1,003 per night
includes taxes & fees
Excellent
(9 reviews)
3-bedroom apartment in charming Boston/ Near Train
Boston
AU$5,141
for 7 nights, 1 apartment
AU$734 per night
includes taxes & fees
Exceptional
(23 reviews)
Brand-new Modern 4BR Boston Comfortable Apartment w/Parking Pet-Friendly - 80/2
Boston
AU$4,864
for 7 nights, 1 apartment
AU$695 per night
includes taxes & fees
Exceptional
(75 reviews)
The Pistachio Room at TPH - Boston
Boston
AU$1,429
for 7 nights, 1 room
AU$204 per night
includes taxes & fees
Exceptional
(49 reviews)
The Inn at Newton Highlands, Suite 2, Apartment-Hotel
Newton
AU$5,225
for 7 nights, 1 apartment
AU$746 per night
includes taxes & fees
Exceptional
(87 reviews)
Special! One of VRBO's Most Popular!! L@@K 1.5 miles to center of Attractions!
Boston
AU$2,339
for 7 nights, 1 apartment
AU$334 per night
includes taxes & fees
Exceptional
(12 reviews)
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
Winthrop
AU$1,999
for 7 nights, 1 apartment
AU$286 per night
includes taxes & fees
Exceptional
(21 reviews)
Cozy Cambridge 2bed 2bath w/ Patio & Parking Pass
Cambridge
AU$5,117
for 7 nights, 1 home
AU$731 per night
includes taxes & fees
Exceptional
(150 reviews)
Maria's JP Rental - Boston Duplex in Popular Jamaica Plain "JP" area
Boston
AU$2,714
for 7 nights, 1 apartment
AU$388 per night
includes taxes & fees
Exceptional
(5 reviews)
Fort Hill Inn-- 2 bedroom Duplex, With a touch of modernity! Minutes to Center
Boston
AU$3,879
for 7 nights, 1 apartment
AU$554 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
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
Historic house renovated for modern convenience
Sleeps 12 · 4 bedrooms · 2 bathrooms
Spacious 4BR Near Green Line, BC & Boston
Sleeps 8 · 4 bedrooms · 1 bathroom
Private Base, #Boston medical #Boston Collage, #The Country Club T+Prk
Sleeps 6 · 3 bedrooms · 1 bathroom
The Pistachio Room at TPH - Boston
Sleeps 2 · 1 bedroom · 1 bathroom
Top rated rentals - Chestnut Hill
Beautiful historic house
Mark's accommodation was excellent, from the fully stocked kitchen to the very comfy beds, felt like being at home. The kitchen had everything (and more) to allow you to cook at home if needed but the place wasn't too far away from restaurants either. The area was very quiet and easy to get to and there was easy parking. There were many books to read and heaps of boardgames that we loved using. My family of 5 adults thoroughly enjoyed our stay and would highly recommend it to other travellers. Thank-you Mark
Danielle T.
Stayed Dec 2023
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 home?
If you're planning a holiday in Chestnut Hill, South Brookline is one of the most in-demand locations to stay. Whatever your style of travel, Stayz is bound to have a property here that matches your needs.
What is the most popular type of holiday home accommodation in Chestnut Hill?
Based on our research, apartments are the most desirable type of holiday home in Chestnut Hill. But naturally, everyone's idea of an awesome trip isn't going to be the same. Stayz has holiday homes in a variety of sizes and shapes, and we'll help you find your ideal fit.
How much does it cost to rent a holiday home in Chestnut Hill?
The average price for a holiday home in Chestnut Hill is determined by a number of factors, including time of year, length of stay and property type. Whether you're dreaming about a sprawling villa with space for extended family or a comfy cabin for just you and the kids, just enter your dates of travel to view stays with fantastic value.
How much does it cost to rent a beach house in Chestnut Hill?
The average price for a holiday home close to the beach in Chestnut Hill depends on when you'll be there and the style and size of property you're looking for. You can find prices easily and quickly on Stayz by entering the dates you'll be travelling. Then make use of the filter tool to choose the number of bedrooms and amenities important to you, such as WiFi, air conditioning and a hot tub.
Are there pet-friendly holiday homes in Chestnut Hill?
You're in luck! There are. You'll have your pick of 13 holiday homes that cater to pets in Chestnut Hill. Lots of our pet-friendly holiday homes even come with an outdoor area for your four-legged friend to run around in, doggie beds, complimentary treats and proximity to parks or green space. Apply the "Pets allowed" filter to find a pad that'll get tails wagging on Stayz.
What are popular home amenities in Chestnut Hill?
A fireplace, an electric car charging station and a firepit are rated the most popular home amenities in Chestnut Hill. Whether you're taking to the road alone, with your sweetheart or a group of dear friends, Stayz can help you find a holiday home that matches your style with all the features you need.
Are there large group holiday homes in Chestnut Hill?
Take your pick of three Stayz properties in Chestnut Hill that can host five or more people. You'll get all the space and privacy you need to have fun with your nearest and dearest — and no one else.
Are there holiday homes in Chestnut Hill that welcome kids?
Chestnut Hill has 13 family-friendly holiday homes. And finding a stay that welcomes youngsters is easy with our "Properties good for families" filter. Besides having the whole place to yourselves, you'll also get access to conveniences and perks such as dining rooms, kitchens and private pools.
What are the top attractions for families in Chestnut Hill?
Keep the kids busy at these top family-friendly attractions in Chestnut Hill:
- Larz Anderson Auto Museum
- Larz Anderson Park
- Coolidge Corner Theatre
Are there one-bedroom holiday homes in Chestnut Hill?
Yes, Chestnut Hill has four one-bedroom homes available. Typically located in prime areas because of their smaller size, a one-bedroom holiday property is ideal if you're travelling with a friend or your partner. And with home comforts such as full kitchens and more privacy than a standard hotel, you'll be able to chill out while sightseeing around this fabulous destination.
Can I find two-bedroom holiday homes in Chestnut Hill?
Chestnut Hill has three two-bedroom holiday homes for you to select from. Discover a holiday home with all the space and comfort you want at a price that's hard to resist on Stayz.
Are there holiday homes with WiFi in Chestnut Hill?
You can pick from four holiday homes with WiFi in Chestnut Hill. If you want to disconnect from daily life while on holiday, but still need to be connected to the web, these getaways are for you. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Chestnut Hill?
You'll have a choice of 12 holiday homes with air conditioning in Chestnut Hill giving you that gentle, cool breeze and extra bit of comfort. Enter your travel dates and then use our filter tool to help you find properties with air conditioning.
How old do you have to be to rent a holiday home in Chestnut Hill?
The minimum age can differ between properties on Stayz, so double-check the rules of the holiday home in Chestnut Hill you want. But typically, it's 16, 18 or 21.
How long can I rent a holiday home in Chestnut Hill for?
The length of time you can book a holiday home in Chestnut Hill differs according to the property. Just enter your preferred travel dates to view a list of options offering extended stays. With plenty of amenities like kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to find someplace just right to call your home away from home in Chestnut Hill.
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