Owner Direct Vacation
Rentals in Wellesley Hills
The Best Owner Direct Vacation Rentals in Wellesley Hills. Explore thousands of vacation home rentals, large cabins, and villas near Wellesley Hills
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Explore the Best Wellesley Hills Vacation Homes
Looking for the perfect place to stay in Wellesley Hills? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Wellesley Hills character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Wellesley Hills Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Wellesley Hills
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Wednesday Jan 28
Wellesley Hills, Wellesley
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Wellesley Hills vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Wellesley Hills
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How to Reserve Your Wellesley Hills Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
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Wellesley Hills Vacation Rental FAQs
1. What are the top vacation rentals in Wellesley Hills?
There are a lot of options in Wellesley Hills. If you plan on staying in the Wellesley Hills area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Wellesley Hills:
- Spacious Private Entrance Master Bedroom/Bath
- Lovely Studio Walk to Wellesley and Babson College
- Beautiful home in Wellesley's Historic district
- Gorgeous, Peaceful Sanctuary on lake minutes from Boston & all local colleges.
- Spacious and lovely 5-bedroom in Wellesley. Only 20 minutes from Boston!
- Wellesley Spacious and Modern
- Elegant Guest Suite Wellesley
- Cozy 1 bedroom in great Wellesley location. 1block from the commuter rail.
- Homewood Suites by Hilton Needham Boston
- 1 Mi to Needham Center Square: Pet-Friendly Apt!
2. Which vacation homes in Wellesley Hills are best for families?
If you are looking for a family-friendly vacation home in Wellesley Hills, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Wellesley Hills:
3. How many vacation rentals are available in Wellesley Hills?
Currently, the total number of properties listed in 2026 is over 38 in the Wellesley Hills area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Wellesley Hills.