
Family-friendly vacation rentals in Raymond
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Top-rated family-friendly rentals in Raymond
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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.

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.

Crow’s Nest Tiny House at Old Crow Ranch
The Crow's Nest Tiny House sits nestled on Old Crow Ranch, a 70-acre working livestock farm, a true example of thriving Maine farmland. You'll be surrounded by fields and pine woods in Durham, Maine. Just outside Freeport and only 30 minutes from Portland, this cozy space makes a calming retreat away from the city - for a night or for a week. Fall asleep listening to the peepers and gazing at the stars, drink your morning coffee while looking out at the cattle grazing in the fields.

Steep Falls Escape, river & falls just steps away
Bright and pleasant 1 bedroom apt with separate entrance, gas fireplace, enclosed porch and large kitchen. Spacious yard to enjoy with pool, fire pit, grill and outdoor seating. Steep Falls is a rural village. Our home is a 5 min walk to the Saco River a favorite destination for canoeing, kayaking or tube floating (after the spring run off!) It is just a 10 min drive to the boat launch for Sebago Lake, one of Maine's largest and most beautiful bodies of water.

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.

The Roost - lovely one bedroom efficiency unit
Staying at the Roost means you will be 15 minutes to the ocean, the airport and to the Old Port; 10 minutes to nearby lakes and rivers; 5 minutes to everything downtown Westbrook has to offer, including many restaurants, parks, live music venues, shopping and a movie theater: what you are looking for is nearby! Kick back and relax in this calm, stylish space with a queen-sized bed, kitchenette, dining/work area, excellent wifi, a full bathroom and a big yard.

Secluded, cozy cabin nestled in the Maine woods
Kick back and relax in this calm, stylish space with a semi-remote cabin experience while keeping the gentle daily living comforts. Right at the edge of the White Mountain National Forest in one direction and in the other direction, a short five minute drive to Kezar Lake this secluded cabin has it all for the nature lover in you! Close to local favorite trailheads for hiking and mountain biking as well having nearby ski mountains and snowmobile trails.

Cozy King bed apt near Portland with free parking
Enjoy a comfortable and relaxing getaway in this charming second-floor studio, owned and operated by a local family. Nestled in a quiet neighborhood, yet just minutes from Downtown Portland with easy access to I-95 and I-295, it offers the perfect mix of peace and convenience. This cozy studio features a brand-new King bed with a fresh mattress and pillows, along with a 3/4 bath—perfect for unwinding after a day of exploring the city or coast.

CloverCroft - "Far from the madding crowd."
CloverCroft, a 200+/- year old farmhouse, is located in the rich farmland of the Saco River Valley at the foot of the White Mountains. We go the extra mile to make your stay enjoyable and comfortable. (Please note our mattress is FIRM and there is a long flight of outdoor stairs to access the suite.) COME ENJOY PRIVACY AND THE GREAT OUTDOORS. There are many summer and winter activities very close by and we look forward to hosting you.

Cozy cottage near Sebago Lake
Cozy & adorable house (cottage) close to Sebago Lake. Backyard with fire pit. Great for those who like boating, swimming, fishing, skiing, snowmobiling. You are close to everything; Sebago Lake State Parks, several areas to launch a boat or visit one of the area beaches (house does not have lake access but plenty of access nearby). Less than 2 miles from grocery stores & restaurants/bars. Sorry no pets!l

Riverfront cabin between Portland & White Mtns.
Look out onto the always-changing Ossipee River from this cute little log cabin. Use our tandem kayak, or fish and swim from our dock. In the winter months, ride your snowmobile right from the driveway, take a brewery tour in Portland, head to the White Mountains, or just watch the river go by. Cornish, Maine is just 12 minutes away and has plenty of dining and shopping opportunities.

Cottage Under a Crabapple Tree
Steps from extensive nature trails and wildflower meadows, this quaint studio cottage is nestled conveniently between the restaurants and breweries of Portland, the outlet shopping of Freeport, and miles and miles of rocky coastline. Perfect for a quiet Maine getaway, lodging near Cumberland fairgrounds and other local attractions, or a visit to family and friends in the area.
Popular amenities for Raymond family-friendly rentals
Family-friendly home rentals with a hot tub

Cottage with Whirlpool tub - McLeod

Hallowell Hilltop Home with Hot Tub & Sauna

Solar Suite surrounded by Nature

LUX Designer Private Waterfront

Cozy Log Cabin mtn views, hot tub, fireplace

Romantic New England Historic Schoolhouse c1866

Cozy Rock Cabin #thewaylifeshouldbe

Amazing Bay View Home with Hot Tub
Family- and pet-friendly home rentals

Zen Den Yurt at Maine Forest Yurts

Luxury Year-round Treehouse with private hot tub

Misty Mountain Hop - minutes to Pleasant Mountain!

Forest Bathing: Off-Grid Tiny Home, Pond w/ Kayak

Sunny 2-BR 5 min to Bates & River Trails

The Misty Mountain Hideout

Mountain View Studio

Dog friendly, lower level apartment off the "Kanc"
Family-friendly home rentals with a pool

Attitash Studio | 5min to Storyland| Pools

Sunny West End Guest Suite w/Harbor Views and Pool

Attitash Retreat

Family friendly + Mountain Views @amountainplace

Cozy Condo at The Seasons- 2 Bedrooms

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

An Amazing Mountain Getaway!

Cozy Family Retreat with Saco River Access
When is the best time to visit Raymond?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R5,078 ZAR | R5,164 ZAR | R4,975 ZAR | R4,975 ZAR | R5,457 ZAR | R5,440 ZAR | R6,628 ZAR | R6,714 ZAR | R5,250 ZAR | R4,527 ZAR | R5,164 ZAR | R5,147 ZAR |
| Avg. temp | -6°C | -4°C | 1°C | 6°C | 12°C | 18°C | 21°C | 20°C | 16°C | 10°C | 4°C | -2°C |
Quick stats about vacation rentals that are family-friendly in Raymond

Total vacation rentals
Explore 220 vacation rentals in Raymond

Nightly prices starting at
Raymond vacation rentals start at R1,721 ZAR per night before taxes and fees

Verified guest reviews
Over 6,010 verified reviews to help you choose

Pet-friendly vacation rentals
Find 80 rentals that welcome pets

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wi-Fi availability
210 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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- Family-friendly rentals Cumberland County
- Family-friendly rentals Maine
- Family-friendly rentals United States
- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Story Land
- Scarborough Beach
- Sunday River Resort
- Popham Beach State Park
- Popham Beach, Phippsburg
- Pemaquid Beach
- East End Beach
- Diana's Baths
- Pemaquid Point Lighthouse
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- King Pine Ski Area
- Willard Beach
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