Vacation rentals in Fresh Pond

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Top-rated vacation rentals in Fresh Pond

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite

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

Jan. 14 – 21

$145 CAD per night

Guest favourite

Apartment in Waltham

4.98 out of 5 average rating, 209 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

Almost every guest describes my place as cozy, which was the feeling I was going for when I designed the space! You will love this large 400 sq. ft private 1 bedroom studio. This unit has a private entrance w/ punch code door, full bathroom, large walk-in closet, mini fridge, freezer and microwave. It has one parking spot in the driveway and a washer /dryer. The backyard is shared but the unit has a private patio. Rental is attached to a single family home. (Please note: No full kitchen)

Dec. 21 – 28

$201 CAD per night

Guest favourite

Guest suite in Watertown

4.99 out of 5 average rating, 207 reviews

Newly Renovated Suite near Boston w/Priv. Bathroom

Spacious in-law suite on 3rd floor of our house conveniently located in Watertown, a few steps away from Harvard Square bus line as well as a 20 minutes drive to downtown Boston. Free parking spot for your car. The main studio has a sitting area, working desk as well as a cozy dining space, with a BONUS separate bedroom and PRIVATE bathroom with shower. NO KITCHEN. When weather permits, you can relax on the balcony and enjoy the sunset while sipping your drinks. We have ample closet space.

Aug. 5 – 12

$266 CAD per night

Guest favourite

Guest suite in Cambridge

4.86 out of 5 average rating, 297 reviews

Convenience, Cozy, and Free Parking

Due to severe allergies that my spouse has, we are UNABLE to host any animals on our property as we share a central AC/heating. Furnished basement STUDIO- cozy, comfortable, and luxurious place- historic neighborhood with peace. Private laundry in the unit-kitchenette, Hi-speed Internet - free parking on street 3/4 min walking to MBTA bus lines 71,74and 75 20 -/+ mins walking to Harvard Square Walking dist to Hospitals, supermarkets, restaurants, cafes, Fresh Pond Lake and Mount A. Cemetery

Jun. 26 – Jul. 3

$261 CAD per night

Guest favourite

Guest suite in Arlington

4.92 out of 5 average rating, 157 reviews

Cozy 1 bed apt Cambridge/Somerville/Arlington line

Our location is only 1.2 miles from Tuffs University and 2.4 from Harvard University. It is in the middle of North Cambridge, Somerville, and Medford. You could walk to Davis Square or to downtown Arlington and will find plenty of good restaurants and coffee places to explore. It is only 3 minutes to public transportation, bus that connects with Red line in the MBTA subway system. Our residential neighborhood is young and vibrant, and excellent point to explore Boston and surrounding towns.

Nov. 16 – 23

$255 CAD per night

Guest favourite

Apartment in Woburn

4.94 out of 5 average rating, 107 reviews

Comfy-Spacious-private 1BR conveniently located

This stylish, private place is perfect for a couple or a small family. Conveniently located minutes from Boston or the north shore whether you are traveling by car, Uber, or local train. Enjoy Boston adventures, north shore excursions, beaches, fall leaf peeping, skiing, historical visits to Massachusetts battle grounds, or some retail therapy at shops and malls nearby. An array of local and city restaurants and breweries provide a multitude of options for your pleasure. YMCA just steps away!

Jan. 16 – 23

$213 CAD per night

Guest favourite

Guest suite in Watertown

4.91 out of 5 average rating, 265 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.

Jan. 3 – 10

$149 CAD per night

Guest favourite

Guest suite in Boston

4.93 out of 5 average rating, 285 reviews

Washer+Dryer+Parking!*Private suite*Cul de sac*

Bright "Spotless" studio in single family home. Airbnb and MA COVID cleaning standards are maintained. Ample on street parking. Peaceful family neighborhood minutes from the green line. Near BU, BC, St. E's, Coolidge Corner, Cleveland Circle, Washington Square. 20 minutes from city center. Ideal for professionals, tourists, student, or visiting parents. Hassle free with all basic amenities. "Micro" kitchen (no stove or oven), Central air, heat, WiFi included. Registered and Licensed Airbnb.

Jun. 24 – Jul. 1

$227 CAD per night

Guest favourite

Guest suite in Peabody

4.98 out of 5 average rating, 177 reviews

Cozy West Peabody Guest Suite

Come enjoy this renovated studio guest suite in the quiet neighborhood of West Peabody! An easy drive to Salem or Boston, close to a woodsy bike trail, and a short drive to local shops and restaurants. Features a fully equipped kitchenette and an outdoor space with a fire pit and charcoal grill. Make use of a Roku TV and fast, reliable WiFi to keep yourself entertained. This is a great space whether you are looking to explore the Boston North Shore or simply embark on a quiet getaway.

Aug. 12 – 19

$187 CAD per night

Guest favourite

Apartment in Arlington

4.98 out of 5 average rating, 174 reviews

Lakeside apartment, patio, hot tub, outside shower

Private apartment, has lock box access, includes bedroom, living room, kitchen & bathroom Private from public, patio and hot tub overlooks lake and conservation land. No stairs Sofa converts to a comfortable queen or twin beds Kitchen is stocked with dishes, pots and pans for 4, coffee and water Hot tub always 104 degrees Kayak, sail boats & swimming available. Portable fire pit $25.00 pet fee Tesla EV charging Covid 19 CDC cleaning and disinfecting procedures are followed

Nov. 12 – 19

$263 CAD per night

Guest favourite

Guest suite in Medford

4.92 out of 5 average rating, 125 reviews

Beautiful 1 Bedroom, 1 Bathroom in Medford

Come stay in this recently renovated, very comfortable space situated in a quiet neighborhood across the street from the Brooks Estate woods, just outside of Boston. The house itself is a historical gothic cottage built in 1856 and is the 2nd oldest home in the area. The space is in a historic single family home and both the bedroom and bathroom are 100% PRIVATE and separated from the rest of the house with a private entrance.

Dec. 4 – 11

$191 CAD per night

Guest favourite

Guest suite in Arlington

4.92 out of 5 average rating, 196 reviews

Modern and comfortable studio apartment

Cozy modern walk-in studio apartment with on-site parking. Located in the Captain Wyman-Pichette House dating from 1840, across from Spy Pond and in Arlington's Historic Pleasant Street district. Steps from public transit to downtown Boston, a short walk to Arlington Center shops, great restaurants and Minuteman Bike Trail. Access to garden patio.

Dec. 12 – 19

$182 CAD per night