
Vacation rentals with outdoor seating in Wellesley
Find and book unique accommodations with outdoor seating on Airbnb
Top-rated accommodations with outdoor seating in Wellesley
Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

All New Private Country Setting (2 Level-No Share)
We built this 2 level home 6 years ago and it is located on Washington St in the towns Historic district. The home is set back from street with a long country style driveway. We designed it with large windows in all rooms, welcoming the sunlight and peaceful setting. Access to clean and empty garage for storage (No parking). We have no personal items in the guest level - all closets and dressers are empty and yours for full use! Co Host reside in lower separate entrance suite. Nothing Shared.

Flower Farm Getaway 2BR, 20 Min To Boston
Spacious two-bedroom in-law suite attached to 1700’s farmhouse, situated on our small flower farm and garden co-op just 20 minutes from Boston. Only a mile from the Mass Pike & Rt. 128 (I-95). Centrally located to all Rt. 128 businesses, colleges & hospitals. A 7-min drive to Riverside Green line “D” subway stop into Boston (parking available), or commuter rail stops (Auburndale, Wellesley & Kendal Green Stations). It's a 20-minute drive to Amtrak's "Route 128" station to NYC and points south.

Peaceful Country Home, Dover, Ma: Private Entrance
Graceful country oasis in a renovated 125 year old historic home, 35 minutes driving time from downtown Boston. (Important-stair climbing required to reach bedroom suite.) I welcome quiet, mature guests as this is a very peaceful (non-party)environment. We are located on a scenic road in sophisticated Dover, Ma, a commuter/country setting, with miles of hiking trails and roads ideal for cycling. I have owned and loved this home for 35 years and take great joy in its charm and outdoor spaces.

Just Renovated, Private & Quiet 2 Bedroom Condo
Keep it simple and comfortable at this peaceful, centrally located getaway. Set at the very end of a private, ultra-quiet dead-end road, the home feels tucked away This newly renovated 2-bedroom unit is an ideal home base for your Boston-area stay You’ll have easy access to public transportation, parks, dining, shopping, and major highways including I-95, I-90, and Route 2. Enjoy your own private outdoor deck, a spacious yard, in-unit laundry, central AC, and off-street parking for two cars

2bed/2bath Apt at Waltham Landing. Middle Unit
This apartment complex was built in 2016. It is 1 block from The Charles River and Waltham's famous Moody Street, aka "Restaurant Row." Across the street from Waltham Station: Fitchburg Line - Commuter Rail. Bentley and Brandeis are 1 mile away. Monthly rentals accepted (inquire for best rate), discounts for groups and long-term rentals. Perfect for business travelers, families, anyone in between housing or visiting town! Free parking in the parking lot. Yes there is an Elevator.

Two bedrooms, full bathroom, and breakfast room
We offer the entire second floor of our home: two bedrooms, each with a queen-size bed, a full bathroom, and a well-stocked breakfast / snack room. We are located literally seconds off Rt. 128 / I-95, in a quiet, secluded area. Our deck, gardens and grounds (which include a pond, birdfeeders, and, perhaps, wildlife sightings) are available for your enjoyment. You will have complete privacy in your quarters, but we will be close at hand should you need advice or service. Gretje and Bob

Entire Historic Carriage House with Fireplace & AC
Escape to our charming Carriage House in the Historic District of Sherborn which offers the feel of a country retreat without being far from civilization. Great for travelers looking for a peaceful getaway, checking out nearby colleges or attending a celebration like a wedding or graduation. You will love the feel of the Carriage House, its spacious living and dining room, well-equipped kitchen, and the beautiful grounds. Check us out on IG @carriagehousema. NEW in 2022: Mini-split AC!

Boston's Luxury Home: Pet-Friendly, 4BR, Sleeps 10
Luxury, modern, bright townhouse offering a gourmet kitchen is available for your next getaway. We are located 1 min walk to Waltham Commuter Rail Station, buses to downtown, famous Moody street & Main street with 50+ restaurants, grocery stores, ALL WITHIN WALKING DISTANCE. Easy commute to anywhere within Waltham, Boston, Cambridge, Watertown. Ideal place for working professionals, families, or someone visiting Boston for the weekend. ATTACHED GARAGE PARKING INCLUDED for 2 cars.

New Super Modern 2 bed in Waltham
A tastefully decorated unit on the 1st floor. Just across from the Waltham Watch Factory. 10-min walk to Moody St. and Charles River path. Built in 2014, open living, dining, and kitchen areas are ideal for working or entertaining. Stainless steel appliances and high class kitchenware. Spacious 2 bedrooms and 1 bathroom. Private deck. In unit washer/dryer. Baby friendly. Parking spot#1. Tax of 11.7% starts 7/1/19. Open and no-contact fire stairway is accessible from the parking lot.

Conveniently Located Private Garden Apartment
Garden-level apartment next to public park, yet convenient to Newton Centre, Chestnut Hill, Boston College, Longwood Medical Area, and public transit. Easy access to Boston area attractions. Sleep late in a comfy bedroom with blackout shades, relax in front of the 55" HDTV, whip up a quick meal in the kitchenette, or enjoy the outdoors sitting on the patio. Come and go as you please with a private entry. Great for quick visits or extended stay. Newton Short Term Rental - STRA-23

Spacious Two Bedroom Apartment
Private and clean renovated 2 bedroom apartment in "Safest Town" in Massachusetts, 25 minutes from Boston. Perfect for families or travelers wanting extra space. Sleeps 6 comfortably in 2 queen beds and 1 futon. Pets are completely welcome! Lots of walking trails nearby. Connected to another unit and shares the large backyard. Lake Chochituate is near with canoe, kayak, and swimming. Close to MassPike, Rt.30 & 27. Close to many colleges and MetroWest office parks.

Private suite 1 BR, 1 BA, 1 LR, 1 FLR
Prime location in Wellesley Hills, MA. Garden level suite offers a living room and a bedroom with a private bath. It offers a full size bed in the bedroom and a queen size pullout sofa in the living room. Private entrance with smart lock entry. Easy access to commuter rail, restaurants, post office, bank, Babson College, Wellesley College and Olin College of Engineering and so much more.
Popular amenities for Wellesley outdoor seating rentals
House rentals with outdoor seating

All the comforts of home, quiet city neighborhood

Harvard House-The Gathering Place.

Stone Cottage with meadow view

Charming Lake Cottage access Boston and Providence

Newly renovated, spacious, clean, 3 bedroom home.

2BR Lovely 1900s Home | 25 Min to Boston | 1200ft²

3 bdrm 2 bath home Walk to the Gillette Stadium

Clean, spacious In-Law Suite -Near Everything
Apartment rentals with outdoor seating

Couples Retreat - Apt in Charming Colonial Home

Light-Filled Luxury Apartment with View

Romantic Getaway w/private Jacuzzi• Fire Pit•

Warm home in Lexington, walk to town, nature trail

Spacious 2 Br with All The Comforts Of Home

Cottage Suite "A" - Walk to Shops, Train, History

3rd FL Apt for 1-4 Guests 15 minutes from Boston

🎖The Ashmont Suite | Close to Subway + Downtown🎖
Condo rentals with outdoor seating

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee

BC/BU - Beautifully Renovated Penthouse 3-BR/2-BA

Spacious, cozy home near Boston!

Fully-Equipped 2nd Floor 1-Bed 1-Bath Apt

Harbor Hideaway

Boho Beach Condo for Ocean Escape

Luxury Condo in Boston w/ backyard & parking

Boston Rooftop Retreat
Quick stats about vacation rentals with outdoor seating in Wellesley

Total vacation rentals
Explore 20 vacation rentals in Wellesley

Nightly prices starting at
Wellesley vacation rentals start at $84 CAD per night before taxes and fees

Verified guest reviews
Over 1,280 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
20 of Wellesley vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Wellesley rentals

4.9 Average rating
Wellesley stays are highly rated by guests—averaging 4.9 out of 5!
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