Vacation rentals in Wellesley

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Top-rated vacation rentals in Wellesley

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Guest favorite

Home in Framingham

4.89 out of 5 average rating, 246 reviews

1BR—Bright & Cozy 2-Level Home — 25 Min to Boston

750sqft One-Bedroom, 2-Level Apartment @ our 3-Rental Property 1st Floor: —Fully Stocked Granite Kitchen w/Dishwasher + Essentials & Cookware —Living Room w/Queen Sofa Bed & Dining Table 2nd Floor: —Bedroom - Queen Memory Foam Bed + Full Length Mirror —Bathroom - Shower/Tub —Desk & Chair + Wardrobe 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 Cleaned & Sanitized/COVID Conscious Host

May 1 – 8

G$33,714 GYD per night

Guest favorite

Guest suite in Weston

5.0 out of 5 average rating, 115 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.

Feb 26 – Mar 5

G$47,457 GYD per night

Guest favorite

Guest suite in Watertown

4.91 out of 5 average rating, 264 reviews

Private 1BR Pied-a-terre

Fully furnished mini-suite with private entrance; walk in at ground level. Picture window view of, and use of, large back yard. Separate sitting and sleeping areas (full size bed), desk/workspace, bathroom with shower, kitchenette with small fridge, coffeemaker and microwave (no stove). Great take-out nearby. No pets, no smoking permitted. Car? There is off-street covered parkling. No car? 71 Bus to Harvard Square stops at our corner; short walk to other buses and public transportation.

Nov 27 – Dec 4

G$19,920 GYD 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

Jan 5 – 12

G$32,470 GYD per night

Guest favorite

Guest suite in Wellesley

4.98 out of 5 average rating, 211 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

G$31,818 GYD per night

Guest favorite

Apartment in Newton

4.91 out of 5 average rating, 265 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.

Jun 9 – 16

G$34,439 GYD 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.

Jan 30 – Feb 6

G$31,179 GYD per night

Guest favorite

Apartment in Hudson

4.85 out of 5 average rating, 293 reviews

Private Mother-In-Law apartment on the lake!

Waterfront on the Lake with a private beach and dock. Relax on your deck and Patio with Wonderful Views. This is a mother-in-law private downstairs apartment complete with kitchen and separate entrance. Enjoy the lake with a fire pit and use of paddle boat and kayaks (life jackets provided). Enjoy the wonderful eclectic restaurants in downtown Hudson including a Micro Brewery, Pub, Martini Bar, Micro Creamery and even a SpeakEasy.

Nov 14 – 21

G$18,225 GYD per night

Guest favorite

Apartment in Newton

4.96 out of 5 average rating, 381 reviews

Sunny apartment in gracious Victorian

Relax into your Boston stay! We offer a sunny in-law apartment on the first floor of a gracious owner-occupied Victorian house. Quiet, safe residential neighborhood. Private entrance. Spacious bedroom, living room with sofabed, kitchenette & bath. Strong Wi-fi. Driveway parking. Contactless check-in, Easy access to Boston, Cambridge, Rts. 128 & 90, and Charles River bike path. Let us welcome you!

Jul 6 – 13

G$35,413 GYD per night

Guest favorite

Guesthouse in Framingham

4.97 out of 5 average rating, 199 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 6 – 13

G$23,106 GYD per night

Guest favorite

Apartment in Natick

4.98 out of 5 average rating, 331 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 19 – 26

G$26,510 GYD 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.

Dec 7 – 14

G$30,989 GYD 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

Guest favorite

Apartment in Framingham

4.95 out of 5 average rating, 181 reviews

Comfortable apartment in Framingham

Jun 23 – 30

G$22,948 GYD per night

Guest favorite

Apartment in Newton

4.88 out of 5 average rating, 105 reviews

Newton Decorator's Guest Suite

Dec 6 – 13

G$33,689 GYD per night

Guest favorite

Guest suite in Sherborn

4.97 out of 5 average rating, 239 reviews

Entire Historic Carriage House with Fireplace & AC

Jul 8 – 15

G$40,926 GYD per night

Superhost

Apartment in Newton

4.85 out of 5 average rating, 123 reviews

Entire Apartment in Newton, Close to Boston!

Sep 19 – 26

G$27,545 GYD per night

Guest favorite

Home in Dedham

4.85 out of 5 average rating, 488 reviews

Private apartment close the city!

G$17,576 GYD 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

G$22,873 GYD per night

Guest favorite

Townhouse in Concord

4.93 out of 5 average rating, 330 reviews

Cottage Suite-Walk to Shops, Train. Town approved.

Jun 18 – 25

G$38,793 GYD 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 13 – 20

G$33,399 GYD 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 320 vacation rentals in Waban, over 50 vacation rentals in Wellesley Square, and over 370 vacation rentals in Wellesley Hills.
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 air conditioning, over 50 homes with free parking, over 50 homes with wifi, over 40 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 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 Framingham

Apartment in Newton

Guest suite in Sherborn

Apartment in Newton

Home in Dedham

Guest suite in Newton

Townhouse in Concord

Apartment in Framingham

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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