Pet-friendly vacation rentals in Raymond

Luxury Year-round Treehouse with private hot tub

Cliff House 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.

Mad Moose Lodge• Secluded Cabin w/ Mountain View’s

Welcome to the Mad Moose Lodge! Year-round adventures begin at this 2-bed, 2.5-bath Stoneham chalet. This vacation rental provides incredible fall foliage views and easy access to mountains and lakes! Close by to cross-country skiing and snowshoeing in the winter and hiking, mountain biking, boating and swimming in the summer there are endless options of outdoor enjoyment. Enjoy stunning sunsets over the mountains from the comfort of the couch, or while enjoying a game of pool in the game room!

Lake House with a View!

Lovely 3 bedroom/2.5 bathroom lakefront house! Watchic Lake is a perfect family destination for swimming, boating, and fishing. Perfectly located for a day trip to Portland, Old Orchard Beach, Kennebunkport, Freeport, Kittery, Wells Beach, and North Conway, NH outlets. Beautiful views of the lake from each room, w/full kitchen, laundry, 3 TVs. As our guest, you will have access to a private boat launch. In the winter snowmobile, snowshoe, ice skates, or cross-country ski on the frozen lake.

The Loons' Nest: Lakefront oasis w/ private dock

Welcome to Maine. Enjoy the peace and tranquility of Maines pristine lakes, at our modern Scandinavian lakefront home. On a PRIVATE lake, nestled in the heart of the Maine countryside. This charming retreat offers a peaceful getaway, perfect for those looking to escape the hustle and bustle of city life. The whole group will enjoy easy access to Maines world famous food scene. Enjoy a private dock with stunning views where you can swim, fish, or launch a host-provided kayak or canoe.

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!

On the water Boathouse!

In the water! Two story boathouse. Originally built in 1939 and parked boats in until 1972. Converted to living space in the early eighties. The upstairs consist of a bedroom walk in closet and a balcony. The downstairs is a living room, kitchen and bathroom. Walk out the door to the patio , dock , and beach! You won't find anything closer to the water! The balcony is the perfect place to watch the sunset, thunderstorms, or sip your morning coffee. Watch the fish out the window!

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!

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.

Charming Victorian farmhouse 1880's bedrooms-2

Victorian farmhouse 1880's Stay in an "era gone by". Private 2 bedroom. Original hardwood floors. Original pocket doors. Sleeps 6. Has living room, kitchen, dinning area 1 bathroom with tub , study area. Charming town, population 4000+. smoke free house. Private keyless entry. The blue door. Free wifi, cable, roku. Has keurig coffee maker with free coffee, dishes, pots, pans, silverware, nu-wave cooktop, toaster, microwave, fridge, pack n play. Queen beds. W & D private.

Paradise in the Lakes Region

Spectacular, expansive, state-of-the-art log cabin—your ultimate four-season escape. Summer fun (beaches & watersports galore), winter ski trips (just 25 minutes to Pleasant Mountain, formerly Shawnee Peak), & unforgettable year-round gatherings. Chef’s kitchen with two ovens, dining for eight + bar seating, sleeps up to 12 (with 2 king beds), two living rooms, and abundant outdoor dining & lounge space, including a playground - designed to make every moment a memory!

Sunset Haven - Little Sebago Lake

Sunset Haven is a beautiful 3BR, 1.5 bath year round lakeside cottage on Little Sebago Lake in Gray, Maine. It boasts a private beach and water frontage in the heart of Maine's Sebago Lakes Region. Located only about half an hour max from Portland, Maine and the Atlantic coastline, approximately an hour or less from Shawnee Peak and the Sunday River Ski areas, 40 minutes from Oxford Casino, this area is truly a great destination for four season recreation.

The Retreat at Crystal Lake Farm

This getaway features two spacious bedrooms plus an upstairs bedroom loft, sleeping up to 6 with ease. The large bathroom is accessed by both the master bedroom and living room and features on-site laundry. For guests who love to cook the kitchen is fully equipped and the deck is a perfect place to relax in the summer and enjoy the view. In colder seasons guests are encouraged to cozy up by the wood-burning stove or use the outdoor BARREL SAUNA.