House holiday rentals in Raymond

Kayak to the Causeway-50s cottage with modern vibe

Find out why the Maine life is the best life at Moonstone Cottage. Play on the shores of Long Lake, stroll the Naples Causeway, eat your way around Portland, and hike the mountains of western Maine before coming home to relax around the fire pit, lounge on the deck, and get a feel for the way life should be. Kayaks are waiting for you on the private association beach, or rent a boat from the marina to explore 40 miles of open water. Restaurants, live music, and the market are a short walk away.

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.

Lake front home on Little Sebago

Relax with up to 8 guests at this peaceful water front cottage. Located on the water, just steps away from Little Sebago’s Upper bay/middle lake area. Enjoy the loons. Sit by the camp fire and roast marshmallows. Take the kayaks out for a paddle or just relax. by the dock. This lake front property offers outdoor space for everyone. ADA compliant ramp in garage and larger doors 1st flr 10 mins from Windham 15 mins from 95 exit in gray 20 mins from Naples (long lake) 40 mins from Portland

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.

Beautiful lake-side home close to Portland Maine

A peaceful & charming renovated old home with private dock on Highland Lake, Falmouth Maine, 20 mins from Portland. *Contact us for longer winter availability! **June/July/Aug, Sat-Sat 7 day min Enjoy beautiful sunsets, canoeing, kayaking, paddle-boarding or fishing on the lake. Or take a short drive to downtown Portland, visit Old Port restaurants & bars, local breweries, Freeport outlet shopping, ski resorts, hiking and walking trails, golf courses, indoor/outdoor cinemas, and more!

Elevated 4-Season home - Mtn Views +A/C + Firepit

Wake up to mountain views, sip coffee on the wrap-around deck, and breathe in the fresh Maine air. At Mountain View Lodge, every detail is designed for you to relax and recharge. Spend your days skiing at Pleasant Mountain, hiking local trails, or floating down the Saco River - and your evenings gathered around the firepit or curled up by the woodstove. With three bedrooms, two baths, and a fully equipped kitchen, there's space for families, friends, and couples to enjoy all four seasons.

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!

Mirror Pond Cottage

A sweet space on a pond, this cottage is perfect for those looking for a quiet getaway. We offer swimming, kayaks and a canoe, life jackets along with a raft to float on. Endless fun in the water, with no motors to be heard. This is a quiet spot and we would hate to be responsible for ruining that. We are family friendly and kids are welcome, but please leave the party at the casino (5 minutes away)! The waterfront is sandy and shallow, perfect for young ones to splash around in.

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

Spacious Lakehouse +Private Dock+Firepit+Kayaks

Welcome to Salmon Point Lodge on beautiful Panther Pond in Raymond, Maine! Nestled on 3 serene acres shared with the friendly owners, this spacious 2,800 sq. ft. home offers the perfect mix of rustic charm and modern comfort. Whether you’re looking for a peaceful getaway or an outdoor adventure, this property has it all including: -Private Dock -Fire Pit -Complementary Kayaks -BBQ Grill -Indoor Fireplace -Ping Pong Table & Board Games -Washer & Dryer -Fully Equipped Kitchen

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!

The Barnhouse with hot tub

Get away with your whole family at this peaceful home in the country. Hear the frogs chirping in the pond, birds tweeting in the treetops and watch chickens roam around. Enjoy the clear, starry nights while relaxing in the hot tub or cozying up by the fire. Centrally located between coast and mountains. Head a hour north to take the family hiking or on the slopes to enjoy the mountains. Head 40 minutes south to take in the coast and see the iconic Maine lighthouse.