Search for vacation rentals in Chestnut Hill.

Whether it's vacation home rentals, apartments, condos, or cabins/cottages, we have you covered -- search for rental properties in the entire Chestnut Hill area to find the perfect spot for your vacay.

478 Clinton Rd
	478 Clinton Rd Chestnut Hill, MA $10 Vacation Rentals, Unknown Single family home with great curb appeal on a cul de sac street, in a top-notch location in close proximity to the renowned Heath school, the Chestnut Hill Reservoir, the B, C and D transportation......

49 Hackensack Rd #49
	49 Hackensack Rd #49 Chestnut Hill, MA $6,500 Vacation Rentals, Unknown Rent $6,500 Avail Date 09/01/2024 Beds-3 Baths-3 Washer/Dryer in Unit No Pets Please Parking is Available, Street Students Ok Laundry in basement, can fit 3 cars in driveway and 2 on street, big......

6 Nelson Dr
	6 Nelson Dr Chestnut Hill, MA $8,000 Vacation Rentals, Unknown Gorgeous & full of natural light, this lovingly remodeled home has been freshly painted outside and inside. Open floor plan with all gleaming hardwood floors, cathedral ceilings, skylights. and......

9 Vine St
	9 Vine St Chestnut Hill, MA $14 Vacation Rentals, Unknown Available Now! Nestled in one of Massachusetts most prominent neighborhoods, this single-family home boasts 5 bedrooms and 5.5 baths. An inviting foyer leads to a formal dining room, while the......

85 Dale St
	85 Dale St Chestnut Hill, MA $5,000 Vacation Rentals, Unknown Rare opportunity to rent this beautiful, freshly painted, 4 bedroom, 2 and 2 half bath single family home with central A/C in the sought after Chestnut Hill neighborhood of Brookline. Two-story......

14 Hammondswood Rd
	14 Hammondswood Rd Chestnut Hill, MA $1,275 Vacation Rentals, Unknown The kitchen overlooks into the living room, perfect for entertainment. The large windows offer light so there is not a need to turn on the light switches. There are also shades to cover the natural......

132 Eliot St
	132 Eliot St Chestnut Hill, MA $9,500 Vacation Rentals, Unknown Available 7/1! Come and check out this beautifully, fully furnished, updated luxurious single-family home, abutting the Hynes School and across from Eliot Playground/Warren field. This property......

830 Newton St
	830 Newton St Chestnut Hill, MA $11 Vacation Rentals, Unknown Beautiful Waban Single Family, Au Pair Suite, MBTA Beautiful Waban Colonial. This magnificent beauty boasts High Ceilings with large windows that allow a ton of natural sunlight. Gleaming hardwood......

37 Eliot St
	37 Eliot St Chestnut Hill, MA $8,500 Vacation Rentals, Unknown Coming Soon! Get on the waiting list to be notified. Beautiful luxury 4 bedroom 3 bathroom bi-level apartment in Chestnut Hill; Brookline School District. Features include an open and spacious......

9 Woodman Rd
	9 Woodman Rd Chestnut Hill, MA $25 Vacation Rentals, Unknown This exceptional home in the desirable Olde Chestnut Hill offers an exquisite interior with ample open spaces for entertaining and family living. The property sits on a gorgeous, well-landscaped......

Woodman Rd
	Woodman Rd Chestnut Hill, MA $25 Vacation Rentals, Unknown This exceptional home in the desirable Olde Chestnut Hill offers an exquisite interior with ample open spaces for entertaining and family living. The property sits on a gorgeous, well-landscaped......

77 Risley Rd
	77 Risley Rd Chestnut Hill, MA $2,100 Vacation Rentals, Unknown Lower level room for rent. 1bedroom 1 living room, 1 bathroom, furniture (bed, table, closet) can be provided. Utilities shared. Great schools, parks nearby. Close to buses and T subways. Quiet and......

367 Newton St
	367 Newton St Chestnut Hill, MA $5,000 Vacation Rentals, Unknown Beautiful mid-century modern home. Large living room and adjacent dining room, both with tall ceilings. A wall of windows offers views of the exceptional screened-in porch and backyard. The kitchen......

90A Bellingham Rd
	90A Bellingham Rd Chestnut Hill, MA $4,800 Vacation Rentals, Unknown Stunning single-family residence conveniently located near Putterham Square in Brookline! Enjoy the convenience of a 5-minute drive to Wegmans and the Chestnut Hill Mall. Tenants are responsible......

90 Bellingham Rd
	90 Bellingham Rd Chestnut Hill, MA $4,800 Vacation Rentals, Unknown Stunning single-family residence conveniently located near Putterham Square in Brookline! Enjoy the convenience of a 5-minute drive to Wegmans and the Chestnut Hill Mall. Tenants are covering all......

170 Middlesex Rd
	170 Middlesex Rd Chestnut Hill, MA $5,800 Vacation Rentals, Unknown Our cozy 2250sqft home in Chestnut Hill has central air. Large yard, very private, near to the Chestnut Hill 'T' Metro stop heading into Boston. This quiet neighborhood has large expensive homes......

234 Bonad Rd
	234 Bonad Rd Chestnut Hill, MA $3,800 Vacation Rentals, Unknown Occupants are still in the house, viewing starts when they move out. Sunny, updated Chestnut Hill brick Tudor on a tree-lined street with garage, au pair suite, expansive deck, level back yard ~ a......

132 Yarmouth Rd
	132 Yarmouth Rd Chestnut Hill, MA $125 Vacation Rentals, Unknown FOR RENT - Luxurious Chestnut Hill estate near the Country Club golf course with ~1 acre of private, lush landscaped grounds + in-ground pool. Custom contemporary details, soaring ceilings,......

232 Woodland Rd
	232 Woodland Rd Chestnut Hill, MA $23 Vacation Rentals, Unknown Stunning BRAND NEW construction brick & slate French Colonial w/ thoughtful architectural detailing. Located on nearly .5 acres in idyllic Chestnut Hill neighborhood, this luxurious home offers 7......

33 Eliot St
	33 Eliot St Chestnut Hill, MA $5,800 Vacation Rentals, Unknown New Kitchen and recently updated Brookline home on quiet tree lined street in great neighborhood. Gumwood Moldings, Fresh Paint, Private Yard, 3 Season Screened Porch with Wood Floor, Very Clean......

24 Crosby Rd
	24 Crosby Rd Chestnut Hill, MA $6,500 Vacation Rentals, Unknown 5 bedroom 2 bathroom available in Newton - Chestnut Hill 09/01/24. Hardwood floors, laundry in unit, driveway parking....

10 Bellingham Rd
	10 Bellingham Rd Chestnut Hill, MA $7,900 Vacation Rentals, Unknown FOR RENT UNFURNISHED - Gorgeous Chestnut Hill detached house with a beautiful private backyard. Located near shops (Chestnut Hill Mall), restaurants, golf course, and park (Larz Anderson Park).......

93 Woodcliff Rd
	93 Woodcliff Rd Chestnut Hill, MA $9,000 Vacation Rentals, Unknown Welcome to your dream home situated in the highly desirable Chestnut Hill neighborhood of Brookline on a quiet street! This 4 bedroom, 3 bath home has it all with an oversized room for office space......

74 Manet Rd
	74 Manet Rd Chestnut Hill, MA $5,800 Vacation Rentals, Unknown 4 bed/ 2 bath located near the heart of BC. Both units are available 2024-2025. 74 Manet was currently under new construction. Updated kitchen and bathrooms. New hardwood floors. Large windows with......

35 Eliot St
	35 Eliot St Chestnut Hill, MA $6,000 Vacation Rentals, Unknown Available now flexible move-in! Updated Home on a Beautiful Tree Lined Street. In the sought-out area of Brookline come and check out this charming deleaded 4 bed, 2 bath spread over 3 levels of......

47 Crosby Rd
	47 Crosby Rd Chestnut Hill, MA $104 Vacation Rentals, Unknown Two fully renovated units on Crosby Road, available for rent individually or as a whole house! Each unit offers four bedrooms and one bathroom, totaling eight bedrooms and two bathrooms. Enjoy......

17 Chestnut Hill Ter
	17 Chestnut Hill Ter Chestnut Hill, MA $149 Vacation Rentals, Unknown Elegant and beautiful home in prime location, Chestnut Hill Terr parcel view of reservoir. The house has been updated to the stud, expanded and rebuild, completed in 2023. Gracious foyer with......

900 W Roxbury Pkwy
	900 W Roxbury Pkwy Chestnut Hill, MA $6,150 Vacation Rentals, Unknown Available NOW! Central Air! Brookline 3 Bed 2.5 Bathroom! With 2 levels of living space and over 2000 Sqft. Steps away from the Brookline Public Library. Please come and check out this luxurious......

378 Russett Rd
	378 Russett Rd Chestnut Hill, MA $4,013 Vacation Rentals, Unknown Offering 2 free months and no Broker fee! Beautiful 2 bed 2 bath options with state of the art new community center and pool access. All unit come with: Open Floor Plans Hardwood floors Brand new......

307 Russett Rd
	307 Russett Rd Chestnut Hill, MA $5,000 Vacation Rentals, Unknown Beautiful, freshly painted, 4 bedrooms, 2.5 bath. Center entrance colonial with open dining and kitchen perfect for entertaining. A guest bedroom off a large and bright living room plus a half bath......

Beautiful 2 Bed 1 Bath Apartment
	Beautiful 2 Bed 1 Bath Apartment Chestnut Hill, MA $1,800 Vacation Rentals, Condo/Townhouse Beautiful apartment in a fantastic location! Excellent management company. Perfect layout for flexible living options....