Vacation Rentals in Woodland Heath, MA: Compare 10+ Sites & Save

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  6.  Woodland Heath

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2138 Best Vacation Rentals in Woodland Heath (Starting from $84)

Sun-filled 1b 1ba W City Views Near Public Trans
Sun-filled 1b 1ba W City Views Near Public Trans
Apartment
Boston, MA, USA
1.8k from Woodland Heath center

Apartments, Accommodations, Pet-friendly, Lodgings, Vacation rentals, Places to stay

1 Bedroom4 Guests
New to Booking
$142
Average price / night
Check Availability
Entire apartment with private entrance.
Entire apartment with private entrance.
Apartment
chestnut hill, MA, 02467, United States
0.1k from Woodland Heath center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
9.4

Superb

68 reviews

$401
Average price / night
Check Availability
Boston Condominium, First Floor Easy Access To Mb
Boston Condominium, First Floor Easy Access To Mb
House
Boston, MA, USA
1.9k from Woodland Heath center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

1 Bedroom4 Guests
New to Booking
$160
Average price / night
Check Availability
Private Base, #Boston medical #Boston Collage, #The Country Club  T+Prk
Private Base, #Boston medical #Boston Collage, #The Country Club T+Prk
House
Brookline, MA, 02467, United States
0.5k from Woodland Heath center

AC, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
9.4

Superb

82 reviews

$446
Average price / night
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Renovated, Sunny, Spacious Studio In Boston
Renovated, Sunny, Spacious Studio In Boston
House
Boston, MA, USA
1.9k from Woodland Heath center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
New to Booking
$84
Average price / night
Check Availability
Chestnut Hill, Parking, Renovated, Book Now!
Chestnut Hill, Parking, Renovated, Book Now!
Apartment
Brookline, MA, 02467, United States
0.9k from Woodland Heath center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

3 Bedrooms8 Guests
New to Booking
$713
Average price / night
Check Availability
Renovated, Chic, one bed, Sleeps 4,Steps to Transit
Renovated, Chic, one bed, Sleeps 4,Steps to Transit
Apartment
Woodland Heath, Chestnut Hill, Massachusetts, USA
1.9k from Woodland Heath center

Pet Friendly, Air Conditioner, Wheelchair Accessible, Parking, Internet, Child Friendly

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$89
Average price / night
Check Availability
Single Family House in Residential Area
Single Family House in Residential Area
House
Brookline, MA, 02445, United States
1.6k from Woodland Heath center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

4 Bedrooms5 Guests
New to Booking
$644
Average price / night
Check Availability
Renovated, Spacious Studio, Near Bc, Bu, Porch
Renovated, Spacious Studio, Near Bc, Bu, Porch
Apartment
Woodland Heath, Chestnut Hill, Massachusetts, USA
2.2k from Woodland Heath center

Apartments, Accommodations, Pet-friendly, 3-star, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
New to Booking
$107
Average price / night
Check Availability
Brookline Family Retreat
Brookline Family Retreat
House
Brookline, MA, 02467, United States
1.6k from Woodland Heath center

AC, Dryer, Free Parking, Heater, Internet, Laundry, Living Area, No Smoking, Washer

4 Bedrooms6 Guests
New to Booking
$464
Average price / night
Check Availability
Gorgeous 5 bedroom Boston Home
Gorgeous 5 bedroom Boston Home
Villa
Chestnut Hill, MA, USA
2.3k from Woodland Heath center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

5 Bedrooms10 Guests
New to Booking
$1325
Average price / night
Check Availability
Renovated 1BED, Steps to MBTA, Shops & Restaurants
Renovated 1BED, Steps to MBTA, Shops & Restaurants
Apartment
Brookline, MA, 02445, United States
1.8k from Woodland Heath center

AC, Crib, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

1 Bedroom4 Guests
10.0

Exceptional

5 reviews

$340
Average price / night
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2 Bed, In Unit Laundry, Boston College, Balcony
2 Bed, In Unit Laundry, Boston College, Balcony
Apartment
Boston, MA, USA
2.5k from Woodland Heath center

Apartments, Cheap, Accommodations, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family, Self-catering

1 Bedroom6 Guests
7.3

Good

4 reviews

$170
Average price / night
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Sun-Filled  w/ City Views public transportation
Sun-Filled w/ City Views public transportation
Apartment
Boston, MA, 02135, United States
1.8k from Woodland Heath center

AC, Crib, Elevator, Extra Bed, Heater, Internet, Kitchen, Microwave, No Smoking

1 Bedroom4 Guests
6.0

Review score

1 reviews

$160
Average price / night
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Queen Anne Brookline B&B
Queen Anne Brookline B&B
House
Brookline, MA, USA
2.6k from Woodland Heath center

Air Conditioner, Internet, Balcony/Terrace, Parking, Sports/Activities, Guest Services, Fireplace/Heating

2 Bedrooms2 Guests
New to Booking
$271
Average price / night
Check Availability
Charming 2-bedroom apartment in Cleveland Circle Boston, Near BC, BU
Charming 2-bedroom apartment in Cleveland Circle Boston, Near BC, BU
Apartment
Boston, MA, 02135, United States
2.0k from Woodland Heath center

No Smoking

2 Bedrooms4 Guests
New to Booking
$115
Average price / night
Check Availability
Boston Vacation,longwood Medical,mins To Mbta,pkg
Boston Vacation,longwood Medical,mins To Mbta,pkg
Apartment
Brookline, MA, USA
2.6k from Woodland Heath center

Apartments, Cheap, Accommodations, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family, Self-catering

1 Bedroom4 Guests
9.0

Fabulous

2 reviews

$211
Average price / night
Check Availability
Sun-filled Unit, Elevator, Pool, Boston College
Sun-filled Unit, Elevator, Pool, Boston College
Apartment
Boston, MA, 02135, United States
2.0k from Woodland Heath center

AC, Barbecue, Crib, Elevator, Free Parking, Heater, Internet, Kitchen, Microwave

1 Bedroom4 Guests
New to Booking
$163
Average price / night
Check Availability
Great 1 Bed Close To Longwd Med, Fenway, Parkng
Great 1 Bed Close To Longwd Med, Fenway, Parkng
Apartment
Brookline, MA, USA
2.6k from Woodland Heath center

Apartments, Accommodations, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Self-catering

1 Bedroom4 Guests
7.0

Good

1 reviews

$176
Average price / night
Check Availability
Quiet, upscale Boston Suburb stay-fast access to Boston hub & hospitals STR25-22
Quiet, upscale Boston Suburb stay-fast access to Boston hub & hospitals STR25-22
House
Newton, MA, 02459, United States
2.2k from Woodland Heath center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms8 Guests
10.0

Exceptional

9 reviews

$828
Average price / night
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Beacon Inn 1750
Beacon Inn 1750
House
1750 Beacon Street, Brookline, MA, 02446, United States
2.2k from Woodland Heath center

AC, Business Services, Fireplace, Heater, Internet, No Smoking, Parking Available, TV

7.4

Good

760 reviews

$122
Average price / night
Check Availability
Sunny,spacious, Sleeps 4, Steps To Mbta,hospitals
Sunny,spacious, Sleeps 4, Steps To Mbta,hospitals
Apartment
Brookline, MA, USA
2.7k from Woodland Heath center

Apartments, Accommodations, Pet-friendly, 3-star, Lodgings, Vacation rentals, Places to stay, Family, Self-catering

5 Bedrooms4 Guests
8.7

Fabulous

3 reviews

$135
Average price / night
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A bright studio in prime commute location, steps aways to metro Green line C&D.
A bright studio in prime commute location, steps aways to metro Green line C&D.
Apartment
Brookline, MA, 02445, United States
2.2k from Woodland Heath center

AC, Free Parking, Internet, Kitchen, No Smoking

8.6

Fabulous

4 reviews

$279
Average price / night
Check Availability
Two Family house 4B3B Newton Center & Green Line
Two Family house 4B3B Newton Center & Green Line
House
Newton, MA, 02459, United States
2.3k from Woodland Heath center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, TV

4 Bedrooms9 Guests
New to Booking
$1147
Average price / night
Check Availability
Steps to public transport, Boston Coll, Roof Deck
Steps to public transport, Boston Coll, Roof Deck
Apartment
Boston, MA, 02135, United States
2.3k from Woodland Heath center

AC, Dryer, Elevator, Extra Bed, Free Parking, Heater, Internet, Laundry, Microwave

1 Bedroom4 Guests
9.0

Fabulous

2 reviews

$160
Average price / night
Check Availability
Cozy 1B, Green Line, Boston Coll, Elev, Roof Deck
Cozy 1B, Green Line, Boston Coll, Elev, Roof Deck
Apartment
Boston, MA, 02135, United States
2.3k from Woodland Heath center

AC, Crib, Elevator, Extra Bed, Free Parking, Heater, Internet, Laundry, Microwave

1 Bedroom4 Guests
New to Booking
$279
Average price / night
Check Availability
Gorgeous Historic Boston Home reg#C0530902070
Gorgeous Historic Boston Home reg#C0530902070
House
Newton, MA, 02467, United States
2.4k from Woodland Heath center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

5 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$1391
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Woodland Heath.

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Frequently Asked Questions

You can explore 2138 verified vacation rentals in Woodland Heath. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Woodland Heath vary depending on the season, property size, and location. Rates typically start from around $84 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Woodland Heath include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Woodland Heath welcome pets. Currently, 47 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Woodland Heath often include amenities such as Fireplace/Heating, Guest Services, and Pet Friendly. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.