Holiday rentals in Raymond

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Top-rated holiday rentals in Raymond

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Top guest favourite

Cottage in Pownal

4.99 out of 5 average rating, 395 reviews

Upscale Timber-Frame Cottage, Shop/Dine/Hike/Bike

Relax and unwind at this cozy post-and-beam cottage in a woodsy setting. Complete with all the modern amenities you will feel at home after exploring all that Maine has to offer. At day’s end ascend to the loft bedroom for a great night's sleep. Please note the current Maine travel restrictions: https://www.maine.gov/covid19 This custom post and beam cottage is brand new. Designed by John Libby, one of the most respected timber frame builders in New England, (www.housesandbarns.com) this space was thoughtfully designed and meticulously built specifically for your enjoyment. This cottage resides on the owner’s property, but is sited on its own two acres nestled among a beautiful stretch of Maine hardwood forest. Accessible via its own private driveway and surrounded by acres of pristine forest, it is the perfect place to relax among nature. No matter the season the exposed weathered Douglas Fir beams of the building will both welcome you and wrap you in a feeling of comfort and contentment. This complete home has all of the amenities. The kitchen includes natural unpolished granite countertops and brand new appliances including a stainless steel gas oven/range, dishwasher and refrigerator. The whitewashed walls of the hallway and bathroom provide a more modern feel, while showcasing all the wonderful knots of the Maine white pine from which it was milled. An easy-to-access, low/no step corner shower complete with floor to ceiling tile and an oversized vanity make time in the bathroom a pleasure. The open concept makes for a natural flow through the space and the sitting area comes complete with a queen sofa bed, TV and a gas fired wood-stove. The vaulted ceilings rise 22’ above the floor providing a spacious and beautiful feel. Radiant heat in the finished concrete floors make the space cozy and keep your feet warm. Oversized and lit stairs lead to the loft where you’ll find a king sized bed providing the opportunity for a great night’s sleep. Large windows make you feel as though your sleeping in the tree tops…come Fall this Oak and Maple forest comes alive with color. A ceiling fan keeps you cool, in the Summer and moves the heat around come Winter. Enjoy the beautiful outdoors on either the front or back deck, or from your own personal fire pit complete with granite bench. Don’t forget the s’mores! Guests have access to the post and beam cottage as well as the immediate surrounding area. We ask that the property boundaries are respected and that the guests do not go past the rock wall or onto the main house property or neighboring properties/horse farm. The post and beam cottage is on the same property as our primary residence but has it’s own driveway and is situated in a private clearing surrounded by beautiful forest. We will usually be available to welcome you personally and are happy to meet new people and make new friends but we also respect our guests privacy as we expect the same in return. Thank you! This post and beam cottage is in the small town of Pownal, 20 minutes from the wonderful restaurants, sights, and sounds of Portland. It's a 10-minute drive to Freeport and the L.L.Bean flagship store. Bradbury Mountain State Park is two miles away.

Guest favourite

Home in Naples

4.99 out of 5 average rating, 124 reviews

LUX Designer Private Waterfront

Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

Guest favourite

Guest suite in Raymond

4.9 out of 5 average rating, 135 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.

Guest favourite

Home in Raymond

5 out of 5 average rating, 16 reviews

Amazing 2bed vaca home with sandy beach!

Welcome to our beautiful home with 150ft of shared beach frontage on amazing sebago lake! This 2 bed 1 bath home has it all. Completely updated with full appliances along with washer and dryer. This home is centeraly located with easy access from the highway. There are endless amounts of options from a day on the beach, hiking trails, skiing, casino, shopping, Portland or the ocean! Also for those who have a boat there's a private launch as well or rentals are walking distance! Come enjoy!

Top guest favourite

Home in Windham

4.94 out of 5 average rating, 140 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

Cabin in Raymond

4.92 out of 5 average rating, 60 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, 82 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, 112 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

Cabin in Raymond

4.93 out of 5 average rating, 154 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.

Guest favourite

Home in Raymond

4.91 out of 5 average rating, 43 reviews

Cottage with private beach access to sebago lake

The Raymond Cottage is the perfect place for Families, couples and nature lovers. Two Bedrooms, fitted with Queen size beds. The House has been freshly renovated in january/february 2023, with all new furniture. 5 minutes from sebago lake, shopping and dining. Just 30 minutes from Portland, this is the perfect place for your Maine vacation. Access to a little private sand beach just 5 min walking distance down our road, it is shared with all on rd. Brand new shower in march 2025

Top guest favourite

Home in Bridgton

5 out of 5 average rating, 103 reviews

Wren Cabin + Wood fired Sauna

We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.

Guest favourite

Home in Raymond

4.94 out of 5 average rating, 69 reviews

Lakehouse Retreat on Jordan Bay, Sebago Lake

Beautiful Lakehouse located on Sebago Lake. A perfect spot to take in the gorgeous lake view w/sandy bottom swimming area. The lake is great for swimming, boating, kayaking, and water activities. Backyard to enjoy lawn games, grill, and relax by the outdoor fire-pit. The house has a cozy modern feel, making a perfect summer vacation or ice fishing/snowmobile trip on the lake. Located within 30 minutes of Portland & Pleasant Mountain Ski Resort.

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Kick off your hiking boots at these rustic lodgings

Popular amenities for Raymond holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Raymond

Guest favourite

Cabin in Naples

4.96 out of 5 average rating, 26 reviews

HotTub, Game Room, LakeFront,Paddleboards & Kayaks

EmilyRating, 5 stars6 days ago

Booked this home to accommodate 7 people. Enough space for everyone. Comfortable sleeping arrangements. Modern appliances, spacious kitchen for us all to be preparing food and drink. Enjoyed being outside by the fire pit and hot tub. Lake was peaceful and fun for us to walk down to and use kayaks and paddle boards. Great spot for a girls getaway for a couple days.

Top guest favourite

Home in Casco

5 out of 5 average rating, 16 reviews

Thomas Pond, Casco Maine

JenniferRating, 5 stars1 week ago

Beautiful house and stay! I have nothing but positive things to say about this home. Great view, very clean, roomy, and activities for the family. Linda was accommodating and responsive, even recommend local restaurants for us to try. We would definitely stay here again.

Home in Gray

5 out of 5 average rating, 3 reviews

The Lazy Hummingbird - Little Sebago home w/ Sauna

NicoleRating, 5 stars3 weeks ago

We loved our time here. The house was clean, well stocked and the bed was comfortable. Unfortunately the weather wasn’t great for paddling while we were there, but that’s where it was so nice to have the sauna to use. The driveway is steeper than we’re used to but it was easy to navigate, especially since it’s on a quiet road with very little traffic. We would definitely recommend this spot to anyone looking for a peaceful escape in the woods.

Guest favourite

Cabin in Raymond

4.96 out of 5 average rating, 189 reviews

Idyllic Lakeside Cabin

NoelleRating, 5 stars2 weeks ago

Me and my friends stay at this cabin was absolutely wonderful. It was very cozy and we all felt right at home. There was enough space for multiple people to stay comfortably. There were many activities provided such as board games, books, corn hole, and canoeing. The fire pit was also great and easy to use. Both of the bathrooms were clean and spacious. Same goes for the rooms, everyone was able to sleep comfortably. Overall, this cabin was perfect for a weekend getaway.

Guest favourite

Cottage in Naples

4.86 out of 5 average rating, 133 reviews

Spring into Summer at Turtle Lane Cottage

JonathanRating, 5 stars4 days ago

My kids and I had a lovely time at Greg's place. It was very clean and comfortable, and plenty of space for cooking, eating, and lounging. We also enjoyed a turtle wandering through the yard. Only suggestion is to bring tissues and shampoo etc. for the shower - we had everything else we needed. Overall a very pleasant stay and we would definitely return!

Top guest favourite

Home in Windham

5 out of 5 average rating, 31 reviews

Maine Vacation Home on the Water

SamRating, 5 stars4 days ago

Kate’s place is in a beautiful location and has so much to do. We loved the wildlife, the easy access to Portland and all the yard games. We can’t wait to come back!

Top guest favourite

Cottage in Windham

5 out of 5 average rating, 79 reviews

Romantic waterfront cottage for two in Maine

MackRating, 5 stars3 weeks ago

We stayed at the cottage for a little celebratory getaway. Although the weather only partially complied, we were amazed by the beautiful views that surrounded the cottage. We spent some time exploring the area and there are some spectacular little gems hidden throughout and around Windham. Maryellen and Bryan were so sweet and made sure to make this stay feel a little closer to home. Definitely a “don’t miss” property!

Guest favourite

Home in Windham

4.83 out of 5 average rating, 6 reviews

Sebago Lake House

SavannahRating, 5 stars2 weeks ago

We stayed here for 5 nights and loved every second of it. Host was responsive when we had questions and was incredibly concise in his answers. It was cold and rainy while we stayed, but it didn’t make the lake any less beautiful! The sound of the rain on the water right outside the windows lulled my entire family and I to sleep. My dad loved the second floor balcony when it wasn’t raining, and the sitting area in the bedroom when it was. House is about 35-40 minutes outside of Portland, which was nice for us, as it meant getting to see the city while still being able to come back to the serene quiet of the house. Kitchen was also a very nice size and we were able to utilize the grill a couple of times as well. Overall, this house was perfect for a quiet getaway.

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Quick stats about holiday rentals in Raymond

Total rentals
260 properties
Nightly prices starting at
₹4,282 before taxes and fees
Total number of reviews
7K reviews
Family-friendly rentals
210 properties are a good fit for families
Pet-friendly rentals
90 properties allow pets
Rentals with dedicated workspaces
120 properties have a dedicated workspace

Holiday rentals in Raymond

Top-rated holiday rentals in Raymond

Holiday rentals for every style

Popular amenities for Raymond holiday rentals

Other great holiday rentals in Raymond

Quick stats about holiday rentals in Raymond

Total rentals

Nightly prices starting at

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with dedicated workspaces

Destinations to explore