Holiday rentals in Wayland

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Top-rated holiday rentals in Wayland

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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

14–21 Jan

$137 SGD per night

Guest favourite

Flat in Framingham

4.92 out of 5 average rating, 259 reviews

Spacious 2 Br with All The Comforts Of Home

This a quaint apartment . Not your typical hotel room. In a country setting but 5-10 minutes from great shopping, restaurants, parks, colleges and major highways. Boston is 22.5 miles away. Fenway Park is 20 miles. Worcester is 17 miles. Private location overlooking conservation land. Walk to great hiking and biking trails but car needed for other activities. Full kitchen, laundry room and living room in addition to 2 br and bath. It has the comfort of a home away from home. Please NO PETS.

12–19 Jan

$214 SGD per night

Guest favourite

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.

22–29 Mar

$304 SGD per night

Guest favourite

Townhouse in Concord

4.93 out of 5 average rating, 330 reviews

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

This is a private unit with no shared areas. It is the front corner of our house and is completely separate. However, you will share walls like in an apartment. Kitchen includes: sink, microwave, fridge, Keurig, and water boiler. Private gated outside lawn and patio. History, nature, dining & shopping are VERY CLOSE. Open and welcoming to ALL types of people. There is a CLEANING FEE in addition to the nightly fee. TV with internet (Prime, Hulu & Netflix) but NO LIVE TV OR CABLE *new furniture

25 Aug – 1 Sep

$239 SGD per night

Guest favourite

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

6–13 May

$209 SGD per night

Guest favourite

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.

8–15 Feb

$207 SGD per night

Guest favourite

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.

18–25 Sep

$203 SGD per night

Guest favourite

Guest suite in Littleton

4.91 out of 5 average rating, 315 reviews

Historic Loft with bathroom & kitchenette

A beautiful 1840s barn loft steps away from miles of hiking trails. Fully separate and private entrance, bathroom, and kitchenette. Enjoy a serene, rustic cabin atmosphere with a historic brick hearth and exposed beams. Southeast facing windows overlook patio, garden and ruins. Off the beaten path but only 5 min. to Rte 2, Rte 495, and Boston commuter rail. Drive times w/o traffic: 45 min. Boston, 20 min. Lowell/ Rte 3, Burlington, Bedford, Nashua 30 min.

3–10 Sep

$144 SGD per night

Guest favourite

Flat 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

25 Jun – 2 Jul

$155 SGD per night

Guest favourite

Flat 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.

12–19 Nov

$120 SGD per night

Guest favourite

Flat in Concord

4.94 out of 5 average rating, 207 reviews

Bishop Suite - Private suite in historic Concord

I live in historic Concord, Massachusetts, 4 miles from Concord Academy, Fenn School, Middlesex School, and many historical sites, and less than 30 miles from downtown Boston. About 4 miles from the commuter rail (train) to downtown Boston, and 2 miles to restaurants, grocery, and any kind of store you would need. For guests staying over 2 weeks, discounts can be negotiated, and an additional $75 cleaning fee will be assessed.

2–9 Jan

$155 SGD per night

Guest favourite

Guest house 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.

10–17 Feb

$151 SGD per night