Waterfront vacation rentals in Raymond

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Top-rated waterfront rentals in Raymond

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Top guest favorite
A serene lake view is depicted, showcasing calm waters reflecting the sky and surrounding trees. A private dock is visible at the water’s edge, adding to the tranquil atmosphere. The natural landscape features a variety of green hues from the trees lining the shore.
Cottage in Raymond
4.92 out of 5 average rating, 124 reviews

Relax by a Quiet Lake

Charming lakeside cottage only 29' from the water on Panther Pond, 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.

Top guest favorite
A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.
Treehouse in Sanford
4.91 out of 5 average rating, 589 reviews

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Top guest favorite
A charming waterfront cottage is presented with a bright blue door and two red chairs on a stone patio. Lush greenery surrounds the property, enhancing its inviting exterior. The tranquil waters of Pettingill Pond can be seen in the background, reflecting the sky.
Home in Windham
4.95 out of 5 average rating, 190 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.

Top guest favorite
Home in Oxford
5 out of 5 average rating, 238 reviews

The Modern Lakehouse

This modern lakehouse is situated on Hogan Pond in Oxford Maine. Here you can stay with all the comforts of a beautiful lakehouse built in 2020 while being feet from the water. This is a great place to vacation whether you prefer the private sandy beach, the A/C inside complete with Smart TV cable and Wifi, or the hottub! Sip a drink at the bar while watching the game or use the grill on the deck but be sure to use the built in sound system to play your music throughout the house and deck.

Top guest favorite
A serene duplex apartment is surrounded by lush greenery, with sunlight filtering through the trees. The exterior features light blue siding, multiple windows, and a neatly maintained lawn. A gravel path leads to a natural area, enhancing the peaceful setting.
Apartment in Gray
4.96 out of 5 average rating, 169 reviews

Two bedroom duplex across st from crystal lake

Relax, have fun, spend quality time with friends and family right here at our quiet little place. Two bedrooms, three beds, one pull out couch, we can accommodate up to six guests. We have walking trails, firepit, and a barbecue area. The house sits across the street from crystal lake, with a boat launch 3/4 mile down the road with a parking area. An easy 20-minute drive to Portland. Supermarket, gas station, and restaurant less than five minutes away and ten minutes from Gray exit to 95.

Guest favorite
A tranquil lakeside scene showcases sandy beach leading to clear water. A boat dock extends into the lake, with boats visible nearby. Lush greenery frames the view, while fluffy clouds float above the water, creating a peaceful atmosphere.
Cottage in Gray
4.81 out of 5 average rating, 106 reviews

Edgewater Retreat - Lakefront w/Sauna & EV Charger

Welcome to Edgewater Retreat! This custom-built cottage features lakefront views and access to three beaches: secluded pocket beach in front of cottage, boaters beach with docks, and a full sun sandy bottom swim beach. Enjoy an unforgettable Maine vacation. Paddlecraft on the water, lounge in the hammocks, S'mores by the campfire, canoe to nearby island for offshore yoga, and gril with friends & family. In winter, enjoy ice fishing and kids enjoy snow sledding on adjacent hill.

Guest favorite
A glamping Geodome stands elevated against a twilight sky, illuminated by warm lights. A small fire burns in a metal pit near a seated figure. Surrounding trees add greenery to the serene outdoor setting, creating a calming atmosphere.
Dome in Buckfield
4.84 out of 5 average rating, 261 reviews

StreamSide Getaway- HOT TUB / AC/ Wi-Fi

The Streamside Getaway offers a luxurious glamping experience in a new solar and wind-powered Geodome. Equipped with custom furniture, new hot tub,luxury appliances, free high speed wifi, AC/Heat Unit and modern bathroom and kitchen facilities, guests can enjoy a homely and comfortable stay in nature. A glamping site built in 2022 offers a contactless check-in process with a custom key code. Additionally, we have added archery, axe throwing, and kayaks to enhance your outdoor activity!

Guest favorite
The cabin exterior is showcased with large glass walls, allowing natural light to fill the interior. A wooden deck is lined with outdoor lights, leading to a hot tub. Surrounded by trees, the peaceful setting is visible, creating a serene outdoor atmosphere.
Home in Naples
4.98 out of 5 average rating, 187 reviews

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

Top guest favorite
A cozy interior features natural wood paneling and beams. Two upholstered chairs are positioned near a large window, allowing light to fill the space. A small bookshelf holds several books, while kitchenware is organized on a nearby shelf. A white stove complements the rustic setting.
Cabin in Bridgton
4.95 out of 5 average rating, 187 reviews

Writers Cabin in the Woods with Sauna!

Nestled in the woods and on Adams Pond with new wood fired sauna! The cabin feels totally hidden away but is less than 10 minutes to Bridgton and Naples, hiking, beaches and restaurants. The woods are beautiful and peaceful and the pond is just down a mossy path. Great for couples or a weekend away. Large deck with grill and outdoor shower, firepit. There is a shared dock on the pond for swimming, fishing, or just enjoying the view as well as a canoe and 2 kayaks, and a paddle board.

Guest favorite
A serene lakeside view reveals a wooden dock with a reclining chair near the water's edge. Vibrant autumn leaves frame the scene, contrasting with the clear blue sky and calm lake. Rocky terrain adds natural texture to the tranquil environment, inviting relaxation.
Cabin in Raymond
4.92 out of 5 average rating, 172 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 eagles 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 favorite
The entrance of a green cabin is framed by snow-covered ground and trees, with a glimpse of a lake visible in the background. A grill is positioned near the steps, and ski equipment leans against the wall, hinting at winter activities.
Cabin in Raymond
4.96 out of 5 average rating, 214 reviews

Idyllic Lakeside Cabin Winter Getaway

Situated on a beautiful lake with 350 feet of private shoreline the cabin is ideal for family gatherings or a small group of friends, it is not available for parties and events. A seven day minimum stay (Saturday to Saturday) is required for July and August. Cozy up with board games, a book and enjoy the tranquility. We have firewood on the property for you to use. The docks are not in the water from October to April.

Top guest favorite
A spacious master bedroom features warm wooden walls and ceiling beams, creating a cozy ambiance. A plush bed is positioned in front of a stone fireplace. Large glass doors invite natural light and provide views of the outdoor space, enhancing the overall serenity.
Guest suite in New Hampshire
5 out of 5 average rating, 200 reviews

A luxury log apartment located on the Saco River

This exquisite log apartment offers a one of a kind luxury experience with a private master bedroom including a gas stone fire place, king bed with exquisite bedding and a balcony which overlooks a 140’ private beach on the Saco River. Also included is a fully equipped designer kitchen/living area with a queen sofa bed, a full spa-like bathroom with a steam shower, Kohler bidet, and soaking tub.

Popular amenities for Raymond waterfront rentals

When is the best time to visit Raymond?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$68,028 GYDG$70,121 GYDG$73,261 GYDG$60,283 GYDG$63,842 GYDG$66,354 GYDG$83,727 GYDG$86,657 GYDG$64,679 GYDG$60,493 GYDG$64,051 GYDG$59,655 GYD
Avg. temp-6°C-4°C1°C6°C12°C18°C21°C20°C16°C10°C4°C-2°C

Quick stats about waterfront rentals in Raymond

  • Total vacation rentals

    Explore 140 vacation rentals in Raymond

  • Nightly prices starting at

    Raymond vacation rentals start at G$25,118 GYD per night before taxes and fees

  • Verified guest reviews

    Over 4,780 verified reviews to help you choose

  • Family-friendly vacation rentals

    130 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    140 of Raymond vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Raymond rentals

  • 4.9 Average rating

    Raymond stays are highly rated by guests—averaging 4.9 out of 5!

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