144+ Vacation Rentals Near The Wayside |
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Cruise Vacations - Vacation Rentals in The Wayside

Wonderfully renovated family-friendly home located near Boston and Lexington From US $440
         

10.0 (75 Reviews)
House
Wonderfully renovated family-friendly home located near Boston and Lexington
  • Air Conditioner
  • Parking
  • TV

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basement Two queen beds with private bathroom in Lexington From US $169
         

9.5 (2 Reviews)
House
basement Two queen beds with private bathroom in Lexington
  • Parking
  • View
  • Security/Safety

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North Bridge Inn From US $218
         

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8.4 (349 Reviews)
Bed & Breakfast
North Bridge Inn
  • Air Conditioner
  • Parking
  • TV

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3 Mi to Minute Man NHP: 'Summer St Retreat' + Deck From US $282
         

10.0 (17 Reviews)
Condo
3 Mi to Minute Man NHP: 'Summer St Retreat' + Deck
  • Air Conditioner
  • Parking
  • TV

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3 Mi to Minute Man NHP Summer St Retreat and Deck From US $291
         

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9.0 (1 Review)
Apartment
3 Mi to Minute Man NHP Summer St Retreat and Deck
  • Parking
  • Accessibility
  • Security/Safety

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Archer Hotel Boston/Burlington From US $166
         

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9.8 (1000 Reviews)
Hotel
Archer Hotel Boston/Burlington
  • Air Conditioner
  • Parking
  • Pool

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Cottage Suite "B" - Walk to Shops, Train, History From US $209
         

10.0 (6 Reviews)
Apartment
Cottage Suite "B" - Walk to Shops, Train, History
  • Air Conditioner
  • Parking
  • TV

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LakeAccess 4 Bed 3 Full Bath HOT TUB From US $750
         

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8.8 (6 Reviews)
Villa
LakeAccess 4 Bed 3 Full Bath HOT TUB
  • Air Conditioner
  • Parking
  • Designated Smoking Area

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The Inn at Hastings Park, Relais & Chateaux - Boston From US $360
         

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9.6 (249 Reviews)
Hotel
The Inn at Hastings Park, Relais & Chateaux - Boston
  • Air Conditioner
  • Pool
  • TV

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18 Mi to Boston - Stylish Unit in Upscale Enclave! From US $1,899
         

10.0 (1 Review)
Apartment
18 Mi to Boston - Stylish Unit in Upscale Enclave!
  • Air Conditioner
  • Parking
  • TV

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Lake Access 4 Bed 3 Full Bath From US $703
         

9.8 (22 Reviews)
House
Lake Access 4 Bed 3 Full Bath
  • Air Conditioner
  • Parking
  • TV

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Spacious vacation townhome unit with a pool From US $302
         

9.8 (17 Reviews)
House
Spacious vacation townhome unit with a pool
  • Air Conditioner
  • Parking
  • Pool

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Cottage Suite "A" - Walk to Shops, Train, History From US $227
         

9.8 (7 Reviews)
Apartment
Cottage Suite "A" - Walk to Shops, Train, History
  • Air Conditioner
  • Parking
  • TV

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✨Private Studio w/Loft Center Historic Carlisle✨ From US $155
         

9.4 (33 Reviews)
House
✨Private Studio w/Loft Center Historic Carlisle✨
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxury 2Bed/1Bath space in house From US $135
         

8.4 (6 Reviews)
House
Luxury 2Bed/1Bath space in house
  • Air Conditioner
  • Parking
  • TV

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18th Century Farm House in Center of Carlisle From US $334
         

8.0 (1 Review)
House
18th Century Farm House in Center of Carlisle
  • Air Conditioner
  • Parking
  • TV

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5-bedroom house in Historic Lexington with cool AC. Near colleges, FIFA, Boston From US $747
         

New
House
5-bedroom house in Historic Lexington with cool AC. Near colleges, FIFA, Boston
  • Air Conditioner
  • Parking
  • TV

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Spacious, Quiet, 4BR+office, 1.5 acres yard From US $311
         

New
House
Spacious, Quiet, 4BR+office, 1.5 acres yard
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxury Apt with Rooftop Terrace and Pool From US $247
         

New
Apartment
Luxury Apt with Rooftop Terrace and Pool
  • Air Conditioner
  • Parking
  • Pet Friendly

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Open Burlington 1BR w/Gym & W/D, nr Dining & Shops, by Blueground From US $142
         

New
Apartment
Open Burlington 1BR w/Gym & W/D, nr Dining & Shops, by Blueground
  • Air Conditioner
  • Parking
  • Pet Friendly

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Tranquility and so close to Boston From US $127
         

New
House
Tranquility and so close to Boston
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

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Mid Century in Historic Lexington From US $320
         

10.0 (59 Reviews)
House
Mid Century in Historic Lexington
  • Air Conditioner
  • Parking
  • TV

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Spacious 1-bedroom apartment in Lexington MA, surrounded by nature trails From US $121
         

10.0 (5 Reviews)
Apartment
Spacious 1-bedroom apartment in Lexington MA, surrounded by nature trails
  • Air Conditioner
  • Parking
  • TV

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Private and Peaceful 4BD Home From US $895
         

10.0 (2 Reviews)
House
Private and Peaceful 4BD Home
  • Air Conditioner
  • Parking
  • TV

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★ Pro Tip: Cruisevacations makes it easy to compare the best listings on Cruisevacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Cruisevacations homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in The Wayside.

Weather in The Wayside

View the weather forecast for The Wayside before booking your The Wayside Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around The Wayside, MA

Cruisevacations offers a large selection of top attractions around The Wayside. Research things to do on your vacation before you visit The Wayside.


Boston College Burlington Mall Tufts University Wellesley College Nashoba Valley Ski Area St. Elizabeth's Medical Center Davis Square Babson College Somerville Theatre Natick Collection Brandeis University Woburn Mall Framingham State University Walden Pond Bentley College Louisa May Alcott's Orchard House Kimball Farm Harvard Law School Old Manse Cochituate State Park

The Wayside Vacation Rental Frequently Asked Questions

How many vacation rentals are available in The Wayside?

Currently, the total number of properties listed in 2026 is over 144 in the The Wayside area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in The Wayside.