Highland Park Cottage Rentals
1593 ft²
6 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $1,398/Night
For 7 Nights US $9,785
1593.06 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- Fireplace/Heating
- Parking
- Air Conditioner
US $498/Night
For 7 Nights US $3,486
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $335/Night
For 7 Nights US $2,347
1206 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Kitchen
- Air Conditioner
- Internet
US $1,315/Night
For 7 Nights US $9,208
1194.79 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Apartment
- Parking
- Air Conditioner
- Internet
US $463/Night
For 7 Nights US $3,241
1399 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $1,241/Night
For 7 Nights US $8,684
193.75 ft²
4 Guests
6 Bedrooms
4 Bathrooms
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $178/Night
For 7 Nights US $1,244
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $136/Night
For 7 Nights US $950
1399.31 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- Fireplace/Heating
- Parking
- Air Conditioner
US $819/Night
For 7 Nights US $5,735
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $674/Night
For 7 Nights US $4,719
1205.56 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Apartment
- Parking
- Air Conditioner
- Internet
US $318/Night
For 7 Nights US $2,226
675 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $287/Night
For 7 Nights US $2,009
Why Choose Rent By Owner for your Highland Park Cottage Rentals?
What makes our Cottage 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.
Weekly Weather Forecast for Highland Park
How to Book Your Highland Park Cottage Rentals
What's our booking process?
Our platform allows you to browse a curated selection of cottage 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 Highland Park
Common Cottage Rentals Amenities
What amenities can you expect?
Our Cottage 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
Highland Park Cottage Rentals Frequently Asked Questions
1. What are the top Cottages in Highland Park?
There are a lot of options in Highland Park. If you plan on staying in the Highland Park area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Cottages in Highland Park:
- Fort Hill Inn- Modern City Triplex !*L@K *Minutes to Center! With Parking!
- *Fresh* Modern Triplex in a Classic Boston Row House, Amazing City Views!
- Cozy Oasis | Near South End
- Bright Brownstone w Terrace+View
- Single family home close to universities and and major hospitals.
- "Fort Hill Inn" Sunny, Penthouse Duplex! L@K 3 bed, 2 bath, 1.5 miles Center
- Essential Boston Home | Near South End
- Cozy Duplex | Near T
- Excellent Hotel Alternative! 1.5 Miles To Center, Fort Hill Inn, Boston
- Stylish, Comfortable Luxury | Near T
2. How many Cottages are available in Highland Park?
Currently, the total number of properties listed by RBO in 2026 is over 64 in the Highland Park area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Highland Park.
More Rentals You May Like Near Highland Park
750 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $248/Night
For 7 Nights US $1,735
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $393/Night
For 7 Nights US $2,749
850 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $248/Night
For 7 Nights US $1,735
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $235/Night
For 7 Nights US $1,642
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $689/Night
For 7 Nights US $4,826
1300 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $410/Night
For 7 Nights US $2,870
5 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $510/Night
For 7 Nights US $3,570
1900 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $564/Night
For 7 Nights US $3,948
5 Guests
2 Bedrooms
1 Bathroom
Condo
- Fireplace/Heating
- Air Conditioner
- Internet
US $253/Night
For 7 Nights US $1,773
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Ocean View
US $172/Night
For 7 Nights US $1,207
3 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Kitchen
US $145/Night
For 7 Nights US $1,014
1 Guest
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $126/Night
For 7 Nights US $885
