
Holiday houses 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.

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 15-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.

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.

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.

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.

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.

Scandi-Modern Apartment
Charming walk-out ground level apartment in a quiet residential neighborhood. Conveniently located west of Boston with easy access to highways. Walkable to grocery store, pharmacy, banks and restaurants. Walk the nearby trail to Lake Cochituate and the Cochituate Rail Trail is less than 1 mile away. Natick Mall is 1.3 miles.

New Markdown! Lovely 3 Bedroom Unit with Garage
This beautiful sunlit second floor unit with private garage has 3 bedrooms, full bathroom, splendid modern kitchen, gracious dining room, an elegant living room and a dedicated pleasant office room . Enjoy the shared backyard with a patio and playground for the kids.
Popular amenities for Wellesley holiday rentals
Other great holiday rentals in Wellesley

Elegant Guest suite Wellesley

Wellesley Spacious and Modern

Modern 2 bedroom

Cozy & Bright Guest Unit

Victorian fully renovated! T station-Boston 20'!

1BR—Peaceful Guest House—20 Min to Boston—Hot Tub

Cozy lakeside retreat

Beautiful New England Home!
When is the best time to visit Wellesley?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $140 AUD | $140 AUD | $151 AUD | $170 AUD | $188 AUD | $168 AUD | $180 AUD | $145 AUD | $140 AUD | $193 AUD | $166 AUD | $140 AUD |
| 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
Where should I stay in Wellesley?
Make yourself at home in Wellesley by choosing from our most frequently booked neighborhoods. We have over 380 vacation rentals in Wellesley Hills, over 340 vacation rentals in Wellesley Farms, and over 340 vacation rentals in Waban.
What are the most popular amenities for House Rentals in Wellesley?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with free parking, over 20 homes with a kitchen, over 40 homes with wifi, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Wellesley have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Wellesley. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Wellesley have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Wellesley. Enjoy a tailored experience with all the comforts you desire.
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.
Do house rentals in Wellesley have free parking?
Absolutely! We offer over 30 house rentals with free parking in Wellesley. Enjoy a tailored experience with all the comforts you desire.
Are there house rentals with a dedicated workspace in Wellesley?
Yes! Work meets play with ease at over 20 house rentals in Wellesley featuring dedicated workspaces. Stay connected and productive in your home away from home.
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.
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 $46 AUD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

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

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- Boston Common
- TD Garden
- Harvard University
- Revere Beach
- Brown University
- Lynn Beach
- New England Aquarium
- Duxbury Beach
- Good Harbor Beach
- Freedom Trail
- MIT Museum
- Canobie Lake Park
- Crane Beach
- Museum of Fine Arts, Boston
- Quincy Market
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- Prudential Center
- Roger Williams Park Zoo
- White Horse Beach
- Salem Willows Park
- Franklin Park Zoo
- Symphony Hall




