
Holiday rentals with outdoor seating in Wellesley
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Wellesley
Guests agree: These Holiday Houses 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.

Comfy Newton Guesthouse
Priced for solo travelers but perfect for 2! Cozy studio, private entrance. Fully furnished w/queen sized bed (memory foam mattress), dresser, a/c, washer/dryer, bathroom with shower stall, closet, high speed Wi-Fi, kitchenette with a small fridge/freezer, griddle, sink, microwave, kettle, toaster, and rice cooker. On-street parking throughout the year on our quiet one-way street, driveway in the winter. Please note that the ceilings are 7 ft tall and shorter in some areas. Cameras outside.

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.

Country Charm minutes from the Hub - 1st Floor Apt
Private, smoke/pet-free 1st floor efficiency apartment with independent access for ONE PERSON ONLY at back of family home. Includes full bathroom, refrigerator, microwave, coffee maker + WiFi. All basic supplies provided. Driveway parking. Mins from MBTA transit including commuter rail. Laundry-room access for rentals of 7 nights ore more. Sorry, no vaping and no smokers - even if you smoke outside - because smoke odor on you or your clothes can be left in your wake in the room. No open flame.

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.

1BR—Bright & Cozy 2-Level Place — 25 Min to Boston
800ft² 1-Bedroom, 2-Level Apartment Private Rental @ our 3-Rental Property 1st Floor: —Fully Equipped Granite Kitchen w/Dishwasher + Essentials & Cookware —Living Room w/Queen Sofa Bed + Dining Table 2nd Floor: —Bedroom - Memory Foam Queen Bed —Full Length Mirror —Desk & Chair + Dresser —Bathroom - Shower/Tub Backyard Patio Laundry Room (Basement) Driveway Parking 25 min to Boston 15 min walk to Train 5 min walk to Jack’s Abby Brewery 3 min walk to Park/Playground Deep Cleaned & Sanitized

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!

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 a public park yet convenient to Newton Centre, Chestnut Hill, Boston College, Longwood Medical Area, and public transit. Easy to take in all the 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.

Private suite 1 BR, 1 BA, 1 LR, 1FLR
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.

Private guest house on beautiful country road
Welcome to Grove Street Studio - our detached guest house which sits right behind our home on one of the most beautiful streets in the area. This two-room studio has everything you need for a comfortable stay including your own deck looking out to the woods behind. Perfect for for a hotel alternative for someone working temporarily at nearby businesses.
Popular amenities for Wellesley outdoor seating rentals
Holiday House Rentals with Outdoor Seating

All the comforts of home, quiet city neighborhood

Updated Antique in Historic Downtown Plymouth

Spacious 4 bedroom home with large yard

Stone Cottage with meadow view

Spacious vacation unit in premium suburban town

The Nest | A peaceful retreat in the city

Large, Comfortable & Conveniently located Home

Renovated Cozy City Getaway
Apartment rentals with outdoor seating

Top Floor luxury Condo

Couples Retreat - Apt in Charming Colonial Home

Light-Filled Luxury Apartment with View

Spacious 2 Br with All The Comforts Of Home

🎖The Ashmont Suite | Close to Subway + Downtown🎖

Garden-level one-bedroom apartment

Short Train 2 Boston, Luxury prvt unit w parking

2 Bdrm Apt w/ tower in JP Victorian
Condo rentals with outdoor seating

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

Charming and Historic Apartment

Boston Rooftop Retreat

Peabody Penthouse Top of the World Sunset View

Quaint Garden Condo one block off Atlantic Ave

Modern Victorian close to Salem
Quick stats about holiday rentals with outdoor seating in Wellesley

Total holiday rentals
Explore 20 holiday rentals in Wellesley

Nightly prices starting at
Wellesley holiday rentals start at $86Â AUD per night before taxes and fees

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

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
20 of Wellesley holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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 a washing machine and dryer Wellesley
- Rentals with a fireplace Wellesley
- Family-friendly rentals Wellesley
- Apartment rentals Wellesley
- House rentals Wellesley
- Rentals with a patio Wellesley
- Rentals with outdoor seating Norfolk County
- Rentals with outdoor seating Massachusetts
- Rentals with outdoor seating United States
- Hampton Beach
- TD Garden
- Fenway Park
- Boston Common
- Harvard University
- Revere Beach
- Brown University
- New England Aquarium
- MIT Museum
- Freedom Trail
- Boston University
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- Prudential Center
- Roger Williams Park Zoo
- Gillette Stadium
- Roxbury Crossing Station
- Boston Children's Museum
- Salem Willows Park




