Holiday rentals in Summerside

4.93 out of 5 average rating, 30 reviews

Modern new duplex in Summerside

Enjoy a stylish experience at this centrally located place in a quiet subdivision in Summerside, PEI. Recently completed new construction (February 2023 landscaping & driveway will be finished in May) with all new furniture, appliances, cookware, BBQ, etc. Great location only 15 min. from the Bridge, 20 min. from Cavendish, 35 min. from Charlottetown and Mill River! Restaurants, shopping 5 min. After all that summer fun, relax on the back deck and watch the sunset on this beautiful island!

4.9 out of 5 average rating, 30 reviews

The Story House - Summerside Restored 3 Bed/2 Bath

The Story House is a lovingly restored 100+ year old treasure of a home. When you walk through the entrance foyer, step back into a simpler way of life. Guests will be charmed by a large eat-in kitchen, dining room, front and back parlors, enclosed front porch, mud room, two full bathrooms, and three bedrooms. Hardwood floors, original trim and unique features throughout. Large, open basement, great for children's play area. Have fun on the large back deck, BBQ patio area, and spacious backyard.

Guest suite in Summerside

4.97 out of 5 average rating, 71 reviews

Orchard House, part of the Lot 19 Cider Company.

The west wing of our heritage home is now available as a self contained apartment for travellers who would like to stay and unwind for a few days, or even longer. There is everything you need! From the private entrance to the fully equipped kitchen/laundry, large sitting room with Cable TV and two large bedrooms with en-suite baths, you will lack for nothing! Our home is circa 1878 and features the architecture of William Critchlow Harris, and lovingly restored over the past 20 years.

5 out of 5 average rating, 31 reviews

Flat in Miscouche

Live Edge Suite

This cozy apartment has everything to make you feel right at home. Newly renovated 1-bedroom ground level apartment with private parking and private entrance. This unit is fully equipped with Bell Fibe TV & internet, new Smart 70” TV, revamped kitchen & living room area, newly renovated bathroom with standup shower and bench. The bedroom is equipped with a queen bed, new hybrid mattress, and a walk in closet with lots of storage. Within a few kms to gas, groceries, and restaurants.

4.97 out of 5 average rating, 72 reviews

Welcoming you to a Cozy Home for an Island Gataway

This 2 bedroom, 2 Bath home is located only 5 minutes to Summerside Boardwalk, parks, trails and restaurants. The home includes a king and a queen bed with air conditioning in both rooms. Take time to relax in the soaker tub after a long day of sightseeing or beach going. Kitchen is fully equipped with everything you may need, which also has air conditioning. Enjoy the large deck with a BBQ and outdoor seating. We look forward to welcoming you to your home away from home.

4.95 out of 5 average rating, 19 reviews

Cottage in Summerside

The Coastal Cowgirl Retreat

Take it easy at this unique and tranquil getaway in Prince Edward Island. With acres of natural trails through the woods to the gorgeous Bedeque Bay (for kayaking, swimming, fishing or clamming, etc) you'll be surrounded by nature and enjoying the simple life 5 minutes to Summerside, 30 min to Charlottetown & Cavendish. We live down the road and will make sure you have everything you need during your stay. Seasonal rental available Oct 2025-June 2026

4.94 out of 5 average rating, 16 reviews

Flat in Linkletter

Private 2BR Haven at Chippers with Garage

Experience comfort and charm at 30 Chippers Street. This 2-bedroom, 2-bathroom unit is conveniently located near amenities in Summerside, PEI. Nestled near the waterfront in a new development, it offers modern amenities and cozy interiors, perfect for families or friends. Enjoy a short drive or bike ride to local cafes and beaches, or relax on the private patio. Ideal for those seeking relaxation and convenience in beautiful Prince Edward Island.

4.89 out of 5 average rating, 119 reviews

Guest house in Albany

Cozy Cottage close to Chelton Beach!

Please join us at our cozy cottage in Chelton, PEI! The cottage has one bedroom, small kitchen, bathroom and private deck. The cottage is nestled on a treed property and is only a three minute walk to a quiet red sand beach. Enjoy the privacy and convenience of this location. The cottage includes parking, is a short drive to Confederation Bridge and is centrally located between Summerside, Charlottetown, and Cavendish.

4.99 out of 5 average rating, 209 reviews

Flat in Summerside

Travellers Rest Apartment

Perfect spot for single or couple for a week or weekend getaway or a business trip with high speed internet or wifi. Fully equipped unit attached but a separate apartment to the main house but totally private. New glass shower, air conditioning and a lovely deck and firepit for those warm evenings. Just the two of us live in the main house so you will have all the privacy you need.

4.98 out of 5 average rating, 54 reviews

Guest Suites at Willowgreen Farm

Take time to relax at this unique and tranquil getaway, located on a farm in the City. The whole house is yours to enjoy while resting from your day of adventuring across the Island, take a walk on the Confederation trail, around the gardens or enjoy a day in, reading in the window nook. Grammies home has always been a place of special times and spoiling…. Come home to the farm.

4.98 out of 5 average rating, 111 reviews

Cottage in Kensington

The Sea Drift by MemoryMakerCottages by the Beach!

Wonderfully spacious beach house with screened in gazebo just steps away from the famous Twin Shores beach and centrally located on the beautiful province of Prince Edward Island boasting breath taking views, world class golf courses and beaches that are second to none. HST included. Open year round. Annually inspected and licensed by Tourism PEI #2101325.