Holiday rentals in Watertown

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Top-rated holiday rentals in Watertown

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

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Guest favourite

Flat 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)

8–15 Dec

$170 SGD per night

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

19–26 Mar

$137 SGD per night

Guest favourite

Guest suite in Newton

4.92 out of 5 average rating, 126 reviews

Sunny 3rd floor Studio - Near Boston

Spacious 3rd floor in-law studio in New England Colonial. NOTE: ACCESS TO STUDIO IS THRU OUR 2nd FLOOR CONDO, WHERE WE LIVE. Studio includes bedroom, bathroom, & living room with sofa bed & work area with large desk. Located in a safe residential neighborhood. A 5 min walk to the Express Bus to Boston City Center, 5 min walk to Whole Foods, Village Cafe, Marty's Wines, & CVS. Close to many Boston universities & colleges. A 20 min drive to Fenway Park. Centrally located for day trip to Cape Cod.

14–21 Jun

$154 SGD per night

Guest favourite

Flat 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!

7–14 Jan

$183 SGD 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.

5–12 Jan

$130 SGD 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.

24 Jun – 1 Jul

$178 SGD per night

Superhost

Flat in Newton

4.85 out of 5 average rating, 124 reviews

Entire Apartment in Newton, Close to Boston!

Come stay in this comfortable one bedroom apartment with large open space living room, kitchen area, bathroom, Wi-Fi, parking, and a private entrance onto a gorgeous backyard garden. Centrally located in a quiet neighborhood equidistant from Moody St. in Waltham and West Newton Sq. -- a 15 minute walk from excellent restaurants and an independent movie theater in both directions. Two dance studios with regular weekend dances nearby. To protect guests with allergies, no pets allowed.

27 Sep – 4 Oct

$179 SGD per night

Guest favourite

Flat in Watertown

4.92 out of 5 average rating, 752 reviews

Luxury 2 Bedroom 2 Bath Suite in Watertown Square

Located in Watertown Square, walking distance to Starbucks, CVS, shops and restaurants. Boston is minutes away. You’ll love our place because no one lives there now, it's absent of all the stuff you'd find in someone's home. This is a really nice, really clean, 1,300 SF suite with 2 bedrooms, 2 full baths and a sleeper sofa. The bus stop to Boston and Harvard Square is across the street, rapid transit takes you to all points in the city. Easy and close major highway access and free parking.

26 Oct – 2 Nov

$463 SGD per night

Guest favourite

Flat in Watertown

4.98 out of 5 average rating, 207 reviews

NEW Modern Apartment Near Boston & Harvard Square.

New modern design apartment located in East Watertown, just a minute away from public transportation to Harvard Square and Downtown Boston. Our one bedroom apartment with queen size bed has a private entrance, a full kitchen, and a pullout sofa in the living room and includes one parking spot. You will feel energized in our freshly finished and tastefully decorated basement apartment and enjoy being very close to many local restaurants and bakeries.

20–27 Dec

$232 SGD 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.

22–29 Jul

$161 SGD 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.

24–31 Dec

$149 SGD per night

Guest favourite

Flat 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.

5–12 Oct

$173 SGD per night