Vacation rentals in Wellesley

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Top-rated vacation rentals in Wellesley

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Top guest favourite
The exterior of a two-level home is depicted, surrounded by lush green lawns and mature trees. A pathway leads to the welcoming entrance, flanked by garden beds featuring various plants. The house features a traditional design with large windows allowing for ample natural light.
Home in Holliston
4.98 out of 5 average rating, 120 reviews

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.

Top guest favourite
A charming farmhouse stands amidst a lush garden, surrounded by vibrant purple irises. The white exterior of the house contrasts beautifully with the greenery, providing a serene atmosphere. Tall trees and a manicured lawn enhance the inviting landscape of the property.
Guest suite in Weston
4.99 out of 5 average rating, 190 reviews

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.

Top guest favourite
A serene bedroom suite features a spacious bed with a light blue quilt, flanked by two windows allowing natural light. A cozy sitting area includes a comfortable couch with patterned pillows, and decorative rugs are placed on the hardwood floor, enhancing the inviting ambiance.
Guest suite in Dover
4.97 out of 5 average rating, 309 reviews

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.

Top guest favourite
A living area features a comfortable sofa with cushions, a glass coffee table, and a flat-screen TV on a stand. A round dining table with wooden stools is visible, along with a large mirror reflecting the space. Sunlight enters through sheer curtains.
Apartment in Waltham
4.97 out of 5 average rating, 102 reviews

Just Renovated, Private & Quiet 2 Bedroom Condo

Keep it simple and comfortable at this peaceful, centrally located getaway. Set at the very end of a private, ultra-quiet dead-end road, the home feels tucked away This newly renovated 2-bedroom unit is an ideal home base for your Boston-area stay You’ll have easy access to public transportation, parks, dining, shopping, and major highways including I-95, I-90, and Route 2. Enjoy your own private outdoor deck, a spacious yard, in-unit laundry, central AC, and off-street parking for two cars

Guest favourite
A dining area is shown with a long wooden table set with neutral placemats. Four tan chairs surround the table, and a decorative flower arrangement is placed at its center. Natural light filters through three large windows, framed by soft gray shades.
Home in West Newton
4.91 out of 5 average rating, 178 reviews

Premium Condo 2B1.5B in Newton 30+ Day Rental Only

Minimum stay is 30 days. This fully furnished 2-3 beds and 2.5 bath duplex condo is ideal for comfortable extended stays. The home offers spacious living areas and flexible sleeping arrangements, suitable for families, professionals, and graduate students seeking stable monthly housing. The upper level includes 2 bedrooms and 1.5 bathrooms, with an additional bedroom and full bath on the lower level available based on occupancy. Utilities and WiFi are included for a convenient long-term stay.

Guest favourite
The kitchen features modern cabinetry with a spacious countertop. Stainless steel appliances, including a refrigerator and microwave, are visible. Four wooden bar stools are positioned around the island, and pendant lighting illuminates the area. The entrance door is seen in the background.
Apartment in Waltham
4.9 out of 5 average rating, 199 reviews

2bed/2bath Apt at Waltham Landing. Middle Unit

This apartment complex was built in 2016. It is 1 block from The Charles River and Waltham's famous Moody Street, aka "Restaurant Row." Across the street from Waltham Station: Fitchburg Line - Commuter Rail. Bentley and Brandeis are 1 mile away. Monthly rentals accepted (inquire for best rate), discounts for groups and long-term rentals. Perfect for business travelers, families, anyone in between housing or visiting town! Free parking in the parking lot. Yes there is an Elevator.

Top guest favourite
The exterior of a red house is framed by a well-maintained garden comprising various flowers and greenery. The house features a welcoming entryway, a chimney, and a grassy area. Sunlight illuminates the scene, highlighting the vibrant colors of the surrounding landscape.
Apartment in Dedham
4.94 out of 5 average rating, 212 reviews

Two bedrooms, full bathroom, and breakfast room

We offer the entire second floor of our home: two bedrooms, each with a queen-size bed, a full bathroom, and a well-stocked breakfast / snack room. We are located literally seconds off Rt. 128 / I-95, in a quiet, secluded area. Our deck, gardens and grounds (which include a pond, birdfeeders, and, perhaps, wildlife sightings) are available for your enjoyment. You will have complete privacy in your quarters, but we will be close at hand should you need advice or service. Gretje and Bob

Top guest favourite
A spacious living area features a vaulted ceiling, large windows allowing natural light, and a comfortable sofa. A wooden coffee table sits at the center, complemented by patterned armchairs. Adjacent, a farmhouse dining table accommodates six, enhancing the open layout.
Place to stay in Sherborn
4.98 out of 5 average rating, 342 reviews

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!

Top guest favourite
A living area features a large wall adorned with natural-themed artwork, complemented by two windows allowing ample light. A flat-screen TV is mounted on the wall opposite a small table with a woven texture. A plush gray sofa enhances the inviting space.
Apartment in Newton Highlands
5 out of 5 average rating, 106 reviews

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.

Guest favourite
A spacious living area features two gray sofas with yellow accent pillows, arranged around a circular wooden coffee table. A gas fireplace is centered against a white mantel, complemented by large windows allowing natural light and views of greenery.
Townhouse in Waltham
4.95 out of 5 average rating, 152 reviews

Boston's Luxury Home: Pet-Friendly, 4BR, Sleeps 10

Luxury, modern, bright townhouse offering a gourmet kitchen is available for your next getaway. We are located 1 min walk to Waltham Commuter Rail Station, buses to downtown, famous Moody street & Main street with 50+ restaurants, grocery stores, ALL WITHIN WALKING DISTANCE. Easy commute to anywhere within Waltham, Boston, Cambridge, Watertown. Ideal place for working professionals, families, or someone visiting Boston for the weekend. ATTACHED GARAGE PARKING INCLUDED for 2 cars.

Superhost
An open living space features a modern gray sofa paired with a dark green accent chair. A round coffee table sits on a textured blue rug. Natural light enters through large windows, illuminating the dining area and kitchen with stainless steel appliances and wooden cabinets.
Condo in Waltham
4.92 out of 5 average rating, 196 reviews

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.

Top guest favourite
A cozy living area is presented with a comfortable gray sofa and a dark wooden coffee table. A small dining table with two chairs is positioned near the patio doors, which are flanked by light curtains. A patterned area rug adds warmth to the hardwood floor.
Apartment in Newton
4.93 out of 5 average rating, 390 reviews

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

Popular amenities for Wellesley vacation rentals

When is the best time to visit Wellesley?

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Frequently Asked Questions

  • 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.

  • 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 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.

  • Where should I stay in Wellesley?

    Make yourself at home in Wellesley by choosing from our most frequently booked neighborhoods. We have over 50 vacation rentals in Wellesley Square, over 340 vacation rentals in Waban, and over 380 vacation rentals in Wellesley Hills.

  • Do house rentals in Wellesley have air conditioning?

    Absolutely! We offer over 50 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 30 house rentals with a kitchen in Wellesley. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Wellesley have wifi?

    Absolutely! We offer over 50 house rentals with wifi in Wellesley. Enjoy a tailored experience with all the comforts you desire.

  • 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.

  • What are the most popular amenities for House Rentals in Wellesley?

    Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with wifi, over 30 homes with a kitchen, over 40 homes with free parking, over 50 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

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 $42 CAD 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 and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    70 of Wellesley vacation 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!