
Vacation rentals in Wellesley
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Top-rated vacation rentals in Wellesley
Guests agree: these stays 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.

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.

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, 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.

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

Elegant Guest suite Wellesley

The 1850 Morse Home with award-winning updates

⭐️Perfect for business travelers & college visits⭐️

Free parking spot – In front of Subway - Location

AKBrownstone: Loft rooftop views by T

1BrApt FreeParking 6minT/Subwy FullKitchn WashDryr

Steps to the Green Line & Minutes from Boston! #38

Cozy lakeside retreat
When is the best time to visit Wellesley?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R1,463 ZAR | R1,463 ZAR | R1,576 ZAR | R1,769 ZAR | R1,962 ZAR | R1,753 ZAR | R1,882 ZAR | R1,512 ZAR | R1,463 ZAR | R2,010 ZAR | R1,737 ZAR | R1,463 ZAR |
| 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 380 vacation rentals in Wellesley Hills, over 50 vacation rentals in Wellesley Square, 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 40 homes with air conditioning, over 40 homes with wifi, over 40 homes with free parking, over 30 homes with a kitchen, 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 vacation rentals in Wellesley

Total vacation rentals
Explore 70 vacation rentals in Wellesley

Nightly prices starting at
Wellesley vacation rentals start at R482 ZAR per night before taxes and fees

Verified guest reviews
Over 3,880 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 of Wellesley vacation rentals include wi-fi 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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