
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.

Stylish 3-bedroom 2- bathroom townhouse
Built in year 1832, formally the Frost High School and Waltham's Town Hall. This urban townhouse has lots of exposed detail and original plank hardwood floors. The first floor has a modern kitchen, open layout, a large bedroom with cathedral ceilings and a king size bed, also the first floor bath features a 4-ft wide shower. The second floor you’ll find a large bedroom with a queen bed. Parallel to that, the suite, comes with a king size power adjustable bed, laundry room and master bathroom.

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.

Cozy en suite w/ high ceilings
 Relax in this peaceful private en suite with breathtaking backyard views of the tall pine forest. Lots of natural light fills the space with room darkening shades to sleep in. Enjoy cozy nights by the fireplace and a well stocked granite kitchen. Great location only minutes to the Mass Pike. 25 min to Boston. 30 min. to Foxboro Stadium. Enjoy shopping at the Natick Mall, AMC movies, tons of diverse dining & grocery options. Backyard has firepit for outdoor eves. Safe walkable neighborhood.

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!

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views
Welcome to our charming 3-bedroom lake cottage in Mendon, MA, where every sunrise paints the sky with breathtaking hues over tranquil waters. Accommodates 6 guests, making it ideal for families or couples seeking serenity. Enjoy lakeside coffee, fishing, kayaking, and evenings by the fire pit. We are pet-friendly, so feel free to bring your dogs along — if you have more than 1 dog, please let us know. Conveniently located near restaurants and attractions. Book now for a magical getaway!

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 vacation unit in premium suburban town
Weston is one of Boston area's most desirable towns. <30 min to downtown Boston with a lot of open space. Centrally located with easy access to highways, train stations, etc. Next to a park with hiking trails, this is a secondary unit (Duplex units) with its own separate entry/exit. 3 bedrooms (one on lower level, two on 2nd level), kitchen, 2 baths (both on lower level). ~2000 square feet of space. Some seasons (including some winters) we have hens in the backyard...

Harvard House-The Gathering Place.
HARVARD HOUSE - The Gathering Place--- Winter Specials for single rooms Jan-March-20% off A magical atmosphere ideal for small weddings, birthdays, graduations, celebrations of life. team building "Harvard House is an amazing place, it helped our family renew the ties that bind." "The team created a shared vision, conflicts got ironed out, we built a rallying momentum." "Our wedding at Harvard House was amazing." "Our group split the costs which made it affordable."

Cozy, historic 3 bedroom home close to Boston!
Welcome to our cozy home. Our place blends historic charm with modern comfort. Enjoy a large, fenced yard with a grill, fire pit, and deck to relax. Inside, you'll find a well-equipped kitchen and a dining room. We offer three bedrooms with comfortable mattresses and soft bedding. The living room has a big TV with cable and streaming apps, plus high-speed Wi-Fi. Families with dogs are warmly welcomed.
Popular amenities for Wellesley outdoor seating rentals
House rentals with outdoor seating

All the comforts of home, quiet city neighborhood

Family Friendly City Oasis! Free Parking, King Bed

Absolutely Gorgeous 3 Bedroom Close to Boston

Stone Cottage with meadow view

Charming Lake Cottage access Boston and Providence

The Nest | A peaceful retreat in the city

Cozy house close to Boston

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

Close to Harvard, MIT & Boston, Gym and Patio!

Your Cozy 1 BR Apt & Relaxing Retreat

Light-Filled Luxury Apartment with View

Quiet, Artistically Decorated Cambridge Apartment

Spacious 2 Br with All The Comforts Of Home

Warm home in Lexington, walk to town, nature trail

Spacious 2BR w/ Free Parking • Steps to Train

Cozy JP Studio-Great Location!
Condo rentals with outdoor seating

A Cozy 3BR Home Close To Train + Boston & Parking

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee

Beautiful, spacious South Boston Condo, Near T

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

Harbor View Suite

Spacious, cozy home near Boston!

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

Samuel Tucker House - Downtown Luxury 2 Bed Condo
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 $82 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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- Rentals with outdoor seating Norfolk County
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- Hampton Beach
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