Family-friendly holiday rentals in Raymond

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Top-rated family-friendly rentals in Raymond

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Guest favourite

Guest suite in New Gloucester

4.98 out of 5 average rating, 173 reviews

Peaceful Lakeside Suite w/Firepit and Kayaks

Open the double doors of your suite for direct access to a beautiful Maine lake. With a private entrance, the open concept apartment is in the walk-out basement of our log-cabin style home. Includes a kitchenette, private bathroom, enclosed unheated porch, large flat screen TV with DirecTV, washer & dryer. A patio with firepit is available (except when snow-covered). You may swim and use our kayaks and other boats, in season, at your own risk. Nice views. Quiet and peaceful. Enjoy star-gazing.

4–9 May

₹9,562 per night

Guest favourite

Home in Bridgton

4.91 out of 5 average rating, 273 reviews

Lake Region Comfort, Close to Everything!

Come enjoy the Highland Lake area known for its clear water, boating and fishing! Just a few miles away from Shawnee Peak which offers both day/night skiing. Also a few miles away is downtown Bridgton where there is the Magic Lantern movie theater and the drive-in theatre. Downtown also offers shopping and many options for superb dining. This single-family residence will provide you with 2 bedrooms, a newly renovated kitchen, sliders to deck, bathroom, living room with large panel tv and WiFi.

1–8 Sep

₹14,409 per night

Guest favourite

Guest house in Conway

4.97 out of 5 average rating, 123 reviews

Private, quiet contemporary studio apartment.

Experience the glory of the seasons from our newly remodeled studio apartment nestled in the woods of New Hampshire’s White Mountains. The apartment has its own private entrance, clean, modern furnishings with a soft contemporary color scheme. We live at the end of a 2.8 mile state designated scenic dirt/gravel road, on 50 acres with a beaver pond, relaxing spaces and colorful gardens. All of this is within 20 minutes of North Conway's shopping and its' majestic mountains, lakes and rivers.

26 Dec – 2 Jan

₹10,170 per night

Guest favourite

Guest house in Harpswell

4.95 out of 5 average rating, 431 reviews

Harpswell Studio on Waterview Property! Lobster!

Attached Cottage Style Studio! Clean, comfy, spacious, colorful and bright! Easy access to Harpswell’s 216 miles of coastline via coastal trails, lovely side roads, small beaches and preserves. Too many trails to count in the surrounding area! Fresh lobster and seafood! Two spectacular state parks with expansive beaches within a scenic 35 minute drive! Just 45 minutes (33 miles) to Coastal Maine Botanical Gardens! Saturday check-in may be available before mid June. Please message us.

30 Sep – 7 Oct

₹11,642 per night

Guest favourite

Cabin in Raymond

4.93 out of 5 average rating, 144 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.

2–9 Oct

₹15,310 per night

Guest favourite

Flat in Lisbon falls

4.95 out of 5 average rating, 383 reviews

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.

16–23 Mar

₹8,098 per night

Guest favourite

Cottage in Brownfield

5.0 out of 5 average rating, 210 reviews

Taproot Cottage at Stone Mountain

Taproot Cottage is cozy, quiet, comfortable and nestled in the beautiful White Mountain foothills of Brownfield, ME. Just one mile from the Stone Mountain Arts Center, 30 minutes to North Conway, NH, and easy access to hiking trails, mountain vistas, and the Lakes Region of western Maine. It offers a well-equipped kitchen/dining/ living room combination, full bath, a relaxing sunroom with full-sized futon for additional sleeping, and a loft bedroom with a queen bed.

7–14 May

₹9,891 per night

Guest favourite

Home in Hollis

4.98 out of 5 average rating, 360 reviews

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

25 Sep – 2 Oct

₹15,226 per night

Guest favourite

Cottage in Gray

4.9 out of 5 average rating, 190 reviews

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.

16–23 Oct

₹21,512 per night

Guest favourite

Home in Cumberland

4.95 out of 5 average rating, 280 reviews

Rustic charm close to Portland

Peaceful and private. My home is a country getaway with unique charm and has a feeling like no other. Just voted the safest town to live in Maine, located close to downtown Portland, the Portland Jet Port, Freeport, beautiful Maine beaches, apple orchards, a Gorgeous wedding venue a mile away called Caswell Farm and close to trails for hiking, my home has many options. It's a great spot for a family to stay and the rental is the entire home.

25 Mar – 1 Apr

₹15,976 per night

Guest favourite

Flat in Freeport

4.91 out of 5 average rating, 195 reviews

1000 sq. ft. 1BR+ Apt Close to Town & Nature

This very spacious and light filled apartment has beautiful views of a marsh and the headwaters of the Harraseeket River. It is also across the street from a 100+ acre bird sanctuary. There is a queen bed in the bedroom, a twin in the large living room, and a twin in a small nook under the eaves off of the kitchen. You can put kayaks in across the street and it is a short 20 minute walk into downtown Freeport. Great year-round location.

8–15 Nov

₹9,255 per night

Guest favourite

Cabin in Raymond

4.96 out of 5 average rating, 164 reviews

Idyllic Lakeside Cabin

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 is required for summer months. 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.

29 Nov – 6 Dec

₹41,457 per night