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

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!

Yurt on Chebeague Island
Imagine staying in a yurt in the woods of Chebeague Island, nestled in a private clearing in the woods. Explore island beaches and hidden trails. This yurt is “glampy” inside with leather chairs and a substantial log bed. The yurt has a rusticator kitchen with all of the basics for cooking: fridge, stovetop, sink, water, firepit & firewood. Outdoor shower. WiFi . Cozy heater for cool spring nights. Ferry options on Casco Bay Lines or CTC Ferry. Host provides transport to/from ferry to the yurt.

Large Loft—Walk to Breweries— Coffee Bar—King Bed
Located on outer Forest Avenue in Portland, Maine, Forest Loft is an impressive, custom built, 1 bedroom / 2 bathroom apartment with vaulted ceilings and plenty of space. Due to its close proximity to the breweries on Industrial Way, Forest Loft commonly welcomes craft beer fans from all over the world. Enjoy the proximity to popular amenities while only a short ride from downtown Portland. MAINE'S TOP HOST OF 2022 https://news.airbnb.com/celebrating-our-top-new-hosts-in-each-us-state-for-2022

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.

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.

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.
Popular amenities for Raymond pet-friendly home rentals
Pet-friendly house rentals

Oak Leaf

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit

The Loons' Nest: Lakefront oasis w/ private dock

Dreamy Mountain Home w/ Hot Tub, Firepit, + Views!

Peaceful Getaway at The Ledges

Spectacular River Retreat with Hiking Trails

Brand New 4BR- fire pit, hot tub, game room.

The ZEN welcomes you, your home away from home.
Pet-friendly home rentals with a pool

Charming Chalet 3 min to SKIING & PVT beach access

Spacious Condo-Attitash Ski-Storyland-Saco & More!

Nordic Village Resort | Highland Top Floor Room

Portland Sweet Escape

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

An Amazing Mountain Getaway!

Steep Falls Escape, river & falls just steps away

OOB Oasis: 5BR Home w/ Private Pool Near Beach
Private, pet-friendly home rentals

Amazing location! Cheerful home near LL Bean

Sebago Lake Cottage | Rare Private Beach & Views

Luxury Barn Retreat-Hot Tub, Firepit & Lake Access

Trickey Moose Family Retreat | Fire Pit Kayaks

Newly Built Studio Apartment

Sebago Lake family friendly escape w dock, dogs ok

Cozy Camp on the lake

The Cloud Cabin
When is the best time to visit Raymond?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $479 CAD | $479 CAD | $410 CAD | $410 CAD | $424 CAD | $498 CAD | $536 CAD | $575 CAD | $423 CAD | $413 CAD | $419 CAD | $438 CAD |
| 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 pet-friendly in Raymond

Total vacation rentals
Explore 90 vacation rentals in Raymond

Nightly prices starting at
Raymond vacation rentals start at $150 CAD per night before taxes and fees

Verified guest reviews
Over 2,550 verified reviews to help you choose

Family-friendly vacation rentals
80 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
90 of Raymond vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Raymond rentals

4.8 Average rating
Raymond stays are highly rated by guests—averaging 4.8 out of 5!
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- Rentals with outdoor seating Raymond
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- Fitness-friendly rentals Raymond
- Rentals with a firepit Raymond
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- House rentals Raymond
- Cabin rentals Raymond
- Rentals with a fireplace Raymond
- Beachfront rentals Raymond
- Rentals with a patio Raymond
- Pet-friendly rentals Cumberland County
- Pet-friendly rentals Maine
- Pet-friendly rentals United States
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Story Land
- Sunday River Resort
- Popham Beach, Phippsburg
- Scarborough Beach
- Popham Beach State Park
- Pemaquid Beach
- Willard Beach
- Pemaquid Point Lighthouse
- East End Beach
- Cape Neddick Beach
- King Pine Ski Area
- Gooch's Beach
- Cranmore Mountain Resort
- Diana's Baths
- Coastal Maine Botanical Gardens
- Crescent Beach State Park
- Wolfe's Neck Woods State Park
- Footbridge Beach
- Funtown Splashtown USA
- Pleasant Mountain Ski Area
- Conway Scenic Railroad




