Vacation rentals in Wellesley

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Top-rated vacation rentals in Wellesley

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Guest favorite

Guest suite in Winchester

5.0 out of 5 average rating, 104 reviews

Warm and cozy 1st flr sweet guest suite w parking

Easy living at this peaceful and centrally-located guest suite. Winchester is the quintessential New England town located just 8 miles from Boston with an easy drive or 16 minute by train from Winchester Center or Wedgemere. Or check out historic Lexington and Concord next door, bustling Arlington Center or hip Davis Square. Tufts University, Harvard Square, Harvard University and MIT nearby. Your comfortable home away from home for fun excursions, get aways, business meeting or college visits

Mar 18 – 25

R1,931 ZAR per night

Guest favorite

Guest suite in Weston

5.0 out of 5 average rating, 116 reviews

FLOWER FARM GETAWAY 2BR 15MIN TO BOSTON

Spacious two-bedroom in-law suite attached to 1700’s farmhouse, situated on our small flower farm and garden co-op just 15 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.

Mar 16 – 23

R4,290 ZAR per night

Guest favorite

Home in Framingham

4.96 out of 5 average rating, 130 reviews

2BR—Charming 1900s Home—1st Floor—25min to Boston

Welcome to our Charming 1900s House! 1st Floor 1200sqft Private Rental @ our 3 Rental Property Sleeps 4 Adults/2 Children Features: Kitchen w/ Dishwasher + Essentials & Cookware Bathroom w/ Tub & Shower 2 Queen Bedrooms w/ Memory Foam Mattresses 1 Queen Memory Foam Sofa-Bed 3 Desks & Chairs Private Entrance Driveway Parking Laundry Room in Basement 25 Min Drive to Boston 15 Min Walk to Train 5 Min Walk to Jack's Abby 3 Min Walk to Playground/Park/Tennis Cleaned & Sanitized / COVID Conscious

May 6 – 13

R2,956 ZAR per night

Guest favorite

Apartment in Newton

4.95 out of 5 average rating, 147 reviews

Sunny, private, comfortable 1 bedroom-convenient.

This listing features a sunny great room. The great room has a large, comfortable couch, TV and desk. Highlights include a modern kitchenette, a new bathroom and air mattress available upon request. The bed is FULL size. You'll have a private stairway that leads to your private entrance. Nice view for sunsets. You have a dedicated parking space. The apartment is in Newton Upper Falls. Close to Mass Pike, route 128 and route 9. It is a 15 minute walk to the Green Line -D route-Eliot Stop

Dec 27 – Jan 3

R2,970 ZAR per night

Guest favorite

Guest suite in Wellesley

4.98 out of 5 average rating, 212 reviews

Spacious Private Entrance Master Bedroom/Bath

Private entrance master bedroom w/exclusive use of attached master bathroom. Studio apartment-like room w/private exterior staircase entrance. Walk to Wellesley College, town center, commuter rail, restaurants, stores, Whole Foods. Short drive to Babson. Sizable room, tasteful decor, king bed, sitting area, microwave, fridge (no TV). High-speed wifi, deck, situated amongst the treetops. Safe suburban neighborhood. Walk/jog trails, tennis courts, walk to spa/gym/yoga w/reasonable day fees.

Feb 8 – 15

R2,925 ZAR per night

Guest favorite

Apartment in Newton

4.91 out of 5 average rating, 266 reviews

Conveniently Located Private Garden Apartment

Garden-level apartment next to a public park yet convenient to Newton Centre, Chestnut Hill, and public transportation. 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 sit on the patio and enjoy the outdoors. Come and go as you please with a private entry. Great for quick visits or extended stays. Please note: Construction next door can be loud during the day.

Oct 2 – 9

R3,166 ZAR per night

Guest favorite

Guest suite in Sherborn

4.98 out of 5 average rating, 240 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!

Jul 17 – 24

R3,974 ZAR per night

Guest favorite

Guest suite in Dover

4.98 out of 5 average rating, 182 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-stairs climbing required to reach bedroom suite.) I welcome quiet, mature guests. 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, and surprisingly close to downtown Boston. I have owned and loved this home for 33 years and take great joy in its charm and outdoor spaces.

Dec 8 – 15

R2,866 ZAR per night

Guest favorite

Apartment in Framingham

4.95 out of 5 average rating, 182 reviews

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

Jul 17 – 24

R2,084 ZAR per night

Guest favorite

Guesthouse in Framingham

4.98 out of 5 average rating, 201 reviews

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.

Nov 13 – 20

R2,127 ZAR per night

Guest favorite

Apartment in Natick

4.98 out of 5 average rating, 332 reviews

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. EV charging available.

Sep 9 – 16

R2,437 ZAR per night

Guest favorite

Loft in Natick

4.99 out of 5 average rating, 174 reviews

Lakeside Studio Loft

Bright, open, private 900 sq foot loft space on Lake Cochituate. This is a mother-in-law suite attached to our lakeside home. This airy studio includes a queen bed, kitchen (no stove or oven) toaster,microwave,hot plate and George Foreman grill, skylit bathroom, living room with television and lakeview deck.

Mar 4 – 11

R2,847 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Wellesley vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Wellesley's top sights

Babson College18 locals recommend

Wellesley College16 locals recommend

Whole Foods Market84 locals recommend

Papa Razzi Wellesley8 locals recommend

The Local Wellesley7 locals recommend

Juniper12 locals recommend

Other great vacation rentals in Wellesley

Superhost

Apartment in Newton

4.85 out of 5 average rating, 124 reviews

Entire Apartment in Newton, Close to Boston!

Aug 22 – 29

R2,531 ZAR per night

Guest favorite

Apartment in Waltham

4.98 out of 5 average rating, 209 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

Jan 8 – 15

R2,396 ZAR per night

Guest favorite

Apartment in Framingham

4.92 out of 5 average rating, 259 reviews

Spacious 2 Br with All The Comforts Of Home

Dec 27 – Jan 3

R3,046 ZAR per night

Guest favorite

Apartment in Hudson

4.85 out of 5 average rating, 293 reviews

Private Mother-In-Law apartment on the lake!

Nov 14 – 21

R1,754 ZAR per night

Guest favorite

Guesthouse in Dedham

4.95 out of 5 average rating, 171 reviews

Country Cottage in the City

Jun 24 – Jul 1

R2,899 ZAR per night

Guest favorite

Guest suite in Newton

4.92 out of 5 average rating, 204 reviews

Private 1 Bedroom suite In West Newton

Aug 6 – 13

R2,400 ZAR per night

Guest favorite

Guest suite in Newton

4.92 out of 5 average rating, 126 reviews

Sunny 3rd floor Studio - Near Boston

Jun 14 – 21

R2,184 ZAR per night

Guest favorite

Guest suite in Littleton

4.91 out of 5 average rating, 315 reviews

Historic Loft with bathroom & kitchenette

Jul 6 – 13

R2,032 ZAR per night

Show all

Quick stats about vacation rentals in Wellesley

Total rentals
70 properties
Wifi availability
70 properties include access to wifi
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
2.6K reviews

Frequently Asked Questions

Do house rentals in Wellesley have free parking?
Absolutely! We offer over 50 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 50 vacation rentals in Wellesley Square, over 370 vacation rentals in Wellesley Hills, and over 320 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 50 homes with free parking, over 50 homes with air conditioning, over 40 homes with a kitchen, over 50 homes with wifi, 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 50 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 50 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 40 house rentals with a kitchen in Wellesley. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Wellesley

Top-rated vacation rentals in Wellesley

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Wellesley vacation rentals

Stay near Wellesley's top sights

Other great vacation rentals in Wellesley

Apartment in Newton

Apartment in Waltham

Apartment in Framingham

Apartment in Hudson

Guesthouse in Dedham

Guest suite in Newton

Guest suite in Newton

Guest suite in Littleton

Quick stats about vacation rentals in Wellesley

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Do house rentals in Wellesley have free parking?

Where should I stay in Wellesley?

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

Are there pet-friendly vacation rentals in Wellesley?

Are there vacation rentals with a dedicated workspace in Wellesley?

Do house rentals in Wellesley have air conditioning?

Do house rentals in Wellesley have wifi?

Do house rentals in Wellesley have a kitchen?

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