
Holiday rentals in Wellesley
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Top-rated holiday rentals in Wellesley
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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.

Cozy Private Studio Unit w/ Laundry and Parking!
Almost every guest describes my place as cozy, which was the feeling I was going for when I designed the space! You'll love this good sized 300 sq. ft PRIVATE 1 bedroom studio. This unit has its own entrance w/ punch code door, full bathroom, large walk-in closet, mini fridge, freezer and microwave. It has one parking spot in the driveway and a washer /dryer. The backyard is shared but the unit has a private patio. Rental is attached to a single family home. (Please note: No full kitchen)

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.

New Super Modern 3 Bed in Waltham
A tastefully decorated unit on the 3rd floor. Just across from 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 3 bedrooms and 2 bathrooms. Private deck. In unit washer/dryer. Parking spot#2. Tax of 11.7% starts 7/1/19. Open and no-contact fire stairway is accessible from the parking lot. Crib available upon request.

2BR Lovely 1900s Home | 25 Min to Boston | 1200ft²
Welcome to our Charming 1900s House! 1200ft² 2nd/Top Floor Private Apartment @ our 3-Rental Property ⭐️Children 12+ Welcome⭐️ Granite Kitchen w/Dishwasher —Fully Equipped w/ Essentials & Cookware Tiled Bathroom w/Bath & Shower 2 Queen Bedrooms 2 Desks & Chairs Recliner Sofa & Glider Loveseat Dining Room for 6 Private Entrance Driveway Parking—2 Spots Laundry in Basement 25 Min Drive to Boston 15 Min Walk to Train 5 Min Walk to Jack's Abby 3 Min Walk to Park Deep Cleaned & Fully 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!

Inn at Newton Highlands, Suite 2, Apartment-Hotel
This gorgeous 1,800 sq. ft. 3 bedroom, 2 1/2 bathroom suite at The Inn at Newton Highlands is impeccably designed and decorated. It occupies the second and third floors of the building and immerses you in luxury and style. Its private 800 sq. ft. deck offers stunning views of the village. The space comes with a bonus room. This suite is one of several luxury suites in a small boutique Inn located in the heart of Newton Highlands in a beautiful , fully remodeled historic building.

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.

Comfortable apartment in Framingham
Newly renovated basement apartment. Private entrance and living space which includes a kitchen, bedroom, hallway and bathroom. The kitchen has a microwave and refrigerator, but no stove. Very clean and well maintained. Comfortable queen size bed. Driveway space for 1 car and plenty of street parking. Great location. Walking distance to Dunkin' Donuts, Domino's Pizza, and local shops. Less than 2 miles from the Mass Pike. No Pets / No Smoking inside

Spacious Private Entrance Master Bedroom/Bath
Private entrance master bedroom w/exclusive use attached bathroom. Studio-like room; exterior staircase entrance. Walk to Wellesley College, town center, commuter rail, restaurants, grocery. Short drive to Babson. Sizable room, tasteful decor, king bed, sofa, microwave, mini-fridge (NO TV/NO KITCHEN). High-speed wifi, deck, view of treetops. Safe suburban neighborhood; good walk trails, walk to tennis/spa/gym/yoga w/reasonable day fees.

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.
Popular amenities for Wellesley holiday rentals
Other great holiday rentals in Wellesley

Arlington Craftsman Blue Room, Int. Well Restored

Spacious Guest Suite/Private Full Bath @Newton

overflow room by Tufts Cambridge Davis Square 闪家@4

Beautiful 2 Bedroom Suite in Home, close to Boston

Great room, beautiful yard and nice neighborhood.

Clean room with Free parking

The Big Back Room. 1 guest only.

private room w/ 2 bed pet friendly
When is the best time to visit Wellesley?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ₹8,200 | ₹8,200 | ₹8,830 | ₹9,912 | ₹10,993 | ₹9,822 | ₹10,542 | ₹8,470 | ₹8,200 | ₹11,263 | ₹9,731 | ₹8,200 |
| Avg. temp | -3°C | -2°C | 2°C | 8°C | 14°C | 19°C | 22°C | 22°C | 18°C | 11°C | 6°C | 0°C |
Frequently Asked Questions
Do house rentals in Wellesley have free parking?
Absolutely! We offer over 40 house rentals with free parking in Wellesley. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Wellesley?
Make yourself at home in Wellesley by choosing from our most frequently booked neighborhoods. We have over 340 vacation rentals in Waban, over 380 vacation rentals in Wellesley Hills, and over 50 vacation rentals in Wellesley Square.
What are the most popular amenities for House Rentals in Wellesley?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with wifi, over 30 homes with a kitchen, over 40 homes with free parking, over 40 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in Wellesley?
Four-legged friends are welcome in Wellesley. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Wellesley?
Yes! Work meets play with ease at over 40 vacation rentals in Wellesley featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Wellesley have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in Wellesley. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Wellesley have wifi?
Absolutely! We offer over 40 house rentals with wifi in Wellesley. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Wellesley have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Wellesley. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Wellesley?
Experience the best of Wellesley with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Wellesley?
Wellesley has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Quick stats about holiday rentals in Wellesley

Total holiday rentals
Explore 60 holiday rentals in Wellesley

Nightly prices starting at
Wellesley holiday rentals start at ₹2,703 per night before taxes and fees

Verified guest reviews
Over 3,670 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
60 of Wellesley holiday rentals include wifi access

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

4.8 Average rating
Wellesley stays are highly rated by guests – averaging 4.8 out of 5!
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- Hampton Beach
- Fenway Park
- TD Garden
- Boston Common
- Harvard University
- Revere Beach
- Brown University
- Lynn Beach
- MIT Museum
- New England Aquarium
- Freedom Trail
- Good Harbor Beach
- Canobie Lake Park
- Duxbury Beach
- Crane Beach
- Museum of Fine Arts, Boston
- Quincy Market
- Prudential Center
- Oakland Beach
- White Horse Beach
- Roger Williams Park Zoo
- Franklin Park Zoo
- Salem Willows Park
- Symphony Hall




