Holiday houses in Raymond

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Top-rated holiday rentals in Raymond

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Top Guest favourite

Home in Raymond

5 out of 5 average rating, 44 reviews

Cheerful Home for your Maine Getaway

Wake up to sounds of birds & enjoy this peaceful Maine home with access to Thomas Pond. Located 45 minutes to Portland, 15 minutes to Windham & just minutes from Jordan Bay on Sebago Lake. Enjoy a summer day on the water; explore the gorgeous fall foliage or take in a local fair; or get in on some winter ice fishing action. Come back to relax in your home away from home after any activity you enjoy! This is the perfect spot to make memories no matter what the season! Your Maine adventure awaits!

Top Guest favourite

Cottage in Raymond

5 out of 5 average rating, 85 reviews

Lovely Lakefront Cottage - Book Your Fall GetAway!

Whether you’re craving a peaceful retreat or a winter adventure, this lakefront cottage has everything you need to create unforgettable memories. Cozy up by the fire, snowshoe the lake, or simply soak in the serene beauty of the season. Embrace the charm of winter on the lake, the perfect getaway for families, couples, or solo adventurers. Don't wait for summer to fall in love with this hidden gem. NOTE: Winter & Spring guests should be comfortable navigating winter weather/seasonal conditions.

Guest favourite

Guest suite in Raymond

4.91 out of 5 average rating, 139 reviews

Rustic knotty pine getaway

lovely completely newly remodeled 2 bedroom 1-1/2 bath completely private upstairs unit with kitchen and private screened in deck. It has a private entrance with plenty of off street parking. located in Maine's lake region area. Walking distance to Raymond beach on Sebago lake. 5 miles to restaurants, shopping and local entertainment. 15 Miles from Portland. 30 to 60 minutes to winter skiing. Kayak, boat, and jet ski rentals nearby. 30 minutes to casino. Electric Vehicle charging on site.

Top Guest favourite

Home in Windham

4.94 out of 5 average rating, 149 reviews

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Guest favourite

Home in Raymond

4.95 out of 5 average rating, 19 reviews

Cozy Family Home w/ Beach Access

Complete remodel with access to a private beach, boat ramp, and dock. This charming open floor plan ranch features 3 bedrooms, 1 bath, fireplace, 1st floor laundry, granite countertops, new appliances, and a lovely porch. Enjoy a large sandy beach area with picnic tables and kayak rack. The water gradually deepens, perfect for families. Close to 2 marinas, a restaurant, and a sandwich shop. Professionally remodeled with all new systems and finishes. Essentially a new home in a prime location.

Guest favourite

Cabin in Raymond

4.92 out of 5 average rating, 63 reviews

Sebago Lake Cottage on Raymond Cape

The Bunk House (450 ftsq). Built for our children and grand children visits. We added a 8 x 12 Screen Room on the front. The entry comes in the Screen Room into the kitchenette/living room. The bedroom has a double bed and bunk beds. There is a bathroom that has a shower, sink, and toilet. This cabin is located 100 ft. behind our home, nestled in the woods. Sebago Lake is down the driveway and across the street. Bring your water toys/use our Paddle Boat/Boards. Water shoes are recommended.

Guest favourite

Guest suite in Raymond

4.95 out of 5 average rating, 86 reviews

Sebago Lake Waterfront Studio

Beautiful Lakehouse studio apartment located on Sebago Lake. A perfect spot to take in the gorgeous lake view w/sandy beach. The lake is great for swimming, boating, kayaking, and water activities. Backyard to enjoy lawn games, grill, and relax by the outdoor fire-pit. This space has a cozy modern feel, for a perfect summer vacation or fall leaf-peeping. Located within 40 minutes of Portland and the beautiful Maine coast. This space is furnished to sleep 4. Dock available for $100 per stay.

Guest favourite

Cottage in Raymond

4.91 out of 5 average rating, 115 reviews

Relax by a Quiet Lake

Charming lakeside cottage only 29' from the waterline, w/65' of private waterfront. The cottage is a 3-season, classic L.C. Andrews, log-sided Maine summer lake home. Cozy atmosphere and a wonderful enclosed porch with amazing waterfront views. Enjoy fishing off the dock, hiking, canoeing, campfire, and exploring surrounding areas. Air conditioning units will ensure your comfort on warm summer nights and high-speed internet will keep your devices connected. Furnishings are family mix.

Superhost

Cottage in Raymond

4.9 out of 5 average rating, 51 reviews

The Great Escape - Picturesque Sebago Lake

Experience an intimate home with stunning Sebago Lake views. This inviting retreat features 4 bedrooms and 8 beds, ensuring a restful stay for up to 12 guests. The enormous kitchen island is perfect for gathering, whether preparing a family feast or enjoying casual conversations. Snuggle up by the propane fireplace in the living area, or spend evenings around the outdoor firepit, making s’mores under the stars. The breathtaking lake views create a serene backdrop for your vacation.

Superhost

Cabin in Raymond

4.93 out of 5 average rating, 158 reviews

Rustic, cozy cabin on Sebago Lake. A hidden gem.

Step out of the screened in patio to lakeside relaxation. Dive into crystal waters, snorkel or float with a cool beverage. Kayak or canoe out to Turtle Cove and enjoy the wildlife in this natural waterway teeming with birds to include our resident Blue Heron, ducks, geese, and loons who make this place their home. We have the fortune of bald eagle pairs in several tall pines. Turtles sunning on doting rocks and lily pads in bloom greet us each day. It is a natural water landscape.

Top Guest favourite

Guesthouse in Windham

4.99 out of 5 average rating, 265 reviews

Cottage on Black Brook Preserve

This charming cottage is thoughtfully furnished, it's your home away from home! Clean and cozy, one bedroom with queen size bed and full kitchen. Sit in front of the gas fireplace or on your own private deck overlooking the 105 acres of Black Brook Preserve. Take a hike, snowshoe or cross-country ski right outside your door. We now have new sofa, bed, refrigerator, stove, as well as shower and bathroom flooring.

Guest favourite

Home in Raymond

4.93 out of 5 average rating, 29 reviews

Farmhouse Chic in the ❤ of the Sebago Lakes Region

Enjoy our remodeled farmhouse just minutes from Maine's best lakes! Relax with family at this peaceful home with a cozy porch & outdoor firepit. Only 11 mi to Sebago Lake State Park. Hike on one of Raymond's 8 hiking trails. Just 13 miles to Naples. Only 35 min to Portland & 1 hour to North Conway, NH.