Guesthouse vacation rentals in Milton

Treehouse in the forest

Treehouse in the Forest is the perfect getaway. Like living at a cottage, minutes away from the city. This place is fully equipped with 2 bedrooms, own kitchenete, and private bathroom. We are just 45 minutes from Toronto with a short drive to both Georgetown & Acton. 10 Minutes to 401. This guesthouse is nestled on a hill with spectacular views, surrounded by 16 acres of towering trees overlooking a creek with a private waterfall and walking trails. Perfect for photographers and influencers.

Location · Value · Parking

The Clayhill Bunkie

Looking for a place to get away that’s semi off-grid or glamping? On The Bruce Trail and minutes from Silvercreek & Terra Cotta Cons. areas, the Credit River, the villages of Glen Williams &Terra Cotta, & Georgetown. Spend your day hiking, cycling, antique hunting, tubing, or site seeing, then order in or grab take-out and come relax by a fire. 1 basket of wood is included, adding great value. You WILL hear wildlife and farm animals here. Rural property, limited electricity, beautiful views.

Family · Location · Walkability

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS JULY 25-31 AUGUST 5-7 (2 nights/3 days) AUGUST 10-29 SEPTEMBER 1-17 Please mark this listing as a favourite to get notifications of last minute deals. Unwind at our cozy guest house. Beautiful 2-bedroom cottage. Enjoy the direct waterfront views from the living room, bedroom and wrap around composite deck. Outdoor fire pit and BBQ. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging. Views from the cottage include orchards and the Lake.

Value · Family · Parking

Melville Guesthouse

Welcome to The Melville Guesthouse, a charming one-bedroom retreat on a quiet street in Elora. Enjoy the privacy of your yard while being a short walk from downtown, the Elora Centre for the Arts, the river, and historic homes. Whether you’re here for trails, boutique shops, or Elora’s arts and dining scene, our standalone guesthouse offers comfort and convenience—perfect for couples and families, with a pull-out couch for extra guests. Ideally located, you’re near everything Elora offers.

Value · Family · Outdoor spaces

Adorable, modern tiny home in Leslieville

Kick back and relax in this calm, stylish space. 10 minute walk to History! 15 minute walk to the beach! Complete with kitchenette, 3 piece bathroom, and an upstairs bedloft (watch your head - 5'3"). There's a queen bed upstairs and a Spaze pullout sofabed downstairs. Rounding out the space is a TV, highspeed internet, and a minisplit ductless AC/heat pump. Linens and towels are provided. Please note steep stairs and low headroom in the loft. Operator Registration STR-2109-FMGHHC.

Family · Value · Amenities

Boutique coach house with Scandinavian Steam Sauna

Morwick Lane - a boutique retreat steps from Hamilton’s best downtown spots, and just an hour from Toronto and Niagara Falls. This restored coach house features curated comforts including a sleek fireplace, luxurious bedding, and a cedar Scandinavian sauna. Enjoy the garden shower after your steam sauna, then unwind in the courtyard with a fireplace and stunning gardens. Perfect for a romantic escape or solo wellness retreat, Morwick Lane invites you to experience something unforgettable.

Location · Family · Breakfast

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

Forget your worries in this quiet,, spacious & serene space. King+queen air/4 twin , lrg patio doors overlooking lush greenery in private backyard oasis. Enjoy in/outdoor living & access to private basketball court, trampoline. Landscaped backyard w deck, bbq, tons of board games, 4K projector (stream from G00gle chromecast) for large screen media / movies, and wine fridge, espresso bar, fridge w ice maker, full bathroom, heated flooring. IMPORTANT: You MUST read “Other Details To Note”

Location · Family · Decor

Carriage House - Elora

Discover a piece of history in Elora, Ontario. This beautiful stone, board & batten private 1-bedroom building was the former carriage house, and is nestled at the rear of the Postmaster's yard. Enjoy the spacious king bed, fireplace, and beautiful garden oasis. Only a 10-minute walk to the downtown. The yard and parking is shared with the Postmaster's House - nothing else is shared! *Please note: the interior space-saving staircase is steep and may not be suitable for all guests*

Family · Value · Indoor spaces

Country Getaway Guest Loft Sleeps 5 people

Relax in this peaceful 2 bedroom 2-bed place in a country setting. Located a few minutes south of Guelph with easy access to the 401. Pearson Airport, Hamilton, Milton, Mississauga, and Kitchener Waterloo are all within 35 minutes. Stroll down the country lane or a nearby trail. Check out a local restaurant – Bistro Reunion, The Danish Place, Change of Pace, Sleemans Brewery, or figure out who did it at the Aberfoyle Mill murder mystery dinner - all within 15 minutes!

Family · Value · Walkability

Bright and Airy Guest Suite with Pool

Large windows, high ceilings, fresh modern decor, cedar sauna, fitness room and backyard pool best describes our Garden Suite. Spoil yourself in everything this space has to offer. Featuring a comfy queen size bed sheeted with luxury cotton and down duvet. A large queen pull-out couch offers space for extra sleepers. Take some time to refine your culinary skills with the well appointed kitchen. Don't overpack, your in-unit washer and dryer will keep your clothes clean.

Location · Family · Condition

The Captain's Cottage at Willow Pond

You will have your own private one bedroom cottage on our 17 acre property. Your countryside getaway can be as quiet or as busy as you make it. You will have access to our tennis court, swimming pool, hot tub, gazebo, pond, garden and woodland trails. Adults are welcome to use the exercise studio. There is a flock of heritage chickens, guinea hens and quail who lay beautiful eggs for your breakfast. We also have bees who produce delicious honey for our guests.

Location · Family · Hot tub

Tiny Home retreat in quiet neighbourhood

Keep it simple at this peaceful, centrally located place. Walking distance to: ~ Elora’s shops ~ sites/ attractions ~festivals ~trails The stocked kitchenette includes: ~Small fridge ~Sink ~Microwave ~Hotplate ~Kettle ~French press for coffee ~toaster ~small blender ~All dishes and cutlery ~EVOO, Vinegar, Salt, pepper, sugar, assorted tea, Regular and decaf coffee Also: ~New Double Bed Mattress (Mar 2025) ~Private patio & seating area ~Free Parking ~Wifi

Value · Family · Nearby