
Vacation rentals in Raymond
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Top-rated vacation rentals in Raymond
Guests agree: these stays are highly rated for location, cleanliness, and more.

Relax by a Quiet Lake
Charming lakeside cottage only 29' from the water on Panther Pond, 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.

Peaceful Lakeside Maine Retreat
Beautiful and peaceful lakeside retreat in Maine. With plenty of space for you and your family or friends to spread out and relax, this fully updated home has all of the features you'll need to enjoy your vacation on the water. Available for winter ice fishing, or get away from it all while working remotely using our reliable WiFi. Only half an hour from Portland's lighthouses and exceptional seafood and craft beer and two hours from Boston. Come and experience Maine - "the way life should be!"

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.

Luxury Year-round Treehouse with private hot tub
Skyframe 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.

Pristine Waterfront Studio Apt. Retreat
Studio apt. on the water where Casco Bay meets the Presumpscot River. Downtown Portland 2 minutes away. Perfect to... *Relax & enjoy the sunset & water views from decks *Head into Portland-Bon Appetite 2018 Restaurant City of the Year & "The Best Lobster Roles in Maine" *CNN named Portland as "one of the best towns to visit in 2024" *Drive up the coast, explore the beautiful beaches, lighthouses, quaint towns *Adventure inland for amazing hikes & mountainous views *Awesome music scene!

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 . Heater for cool spring nights. Ferry options on Casco Bay Lines or CTC Ferry. Host provides transport to/from ferry to the yurt.

Tree Yurt
The Tree Yurt is quite literally a yurt in the trees. Surrounded by nature, this is YEAR ROUND GLAMPING close to Portland. Water for the outdoor shower and outdoor sink is seasonal Typically May through October. We do provide water for colder months. A main house sits closer to the driveway and There is a chance the house and the yurt will be rented out at the same time. The yurt is about 200 feet from the house and the only shared space is the driveway, so it is actually very private :)

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.

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!

The Loon's Nest Cottage
Located only 30 minutes from Portland this adorable and cozy cottage sits 10 feet from Watchic Lake. Listen to the loons all day, paddle to an island, stare at the glassy lake from the breakfast nook, swim forever, read a book in the screened-in porch or toast marshmallows in the firepit, whichever it may be you'll simply enjoy the peace and tranquility of this very private Maine lake house nestled in the woods. If you’re feeling like a hike, a dinner out there are options a plenty!

The Maine Frame | Modern A-Frame Cabin in Freeport
• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

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 eagles in several tall pines. Turtles sunning on doting rocks and lily pads in bloom greet us each day. It is a natural water landscape.
Popular amenities for Raymond vacation rentals
Stay near Raymond's top sights
Raymond house rentals

Cozy cottage near Sebago Lake

Mirror Pond Cottage

Beautiful +Nostalgic + Coastal Maine Cottage

Modern 4-Season Escape w/ Mtn Views, A/C & Firepit

The LOTUS welcomes you, stay a while

Historic, pastoral home in charming Yarmouth, ME!

Lake Region Comfort, Close to Everything!

Paradise in the Lakes Region
Lakefront house rentals in Raymond

Private Beach Retreat: Big Yard + Dogs Welcome

Lakefront Getaway

Lakehouse Retreat on Jordan Bay, Sebago Lake

Fish Tales Cabin

Beautiful lake-side home close to Portland Maine

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit

Stunning Bridgton Lake House with EV charger

Lake front home on Little Sebago
Other great vacation rentals in Raymond

Treehouse With Hot Tub Close to Sunday River!

Spacious rural home with hot tub on the deck

Maple Moon Farm, stay at a historic Maine farm! 1

On the water Boathouse!

Wren Cabin + Wood fired Sauna

Sanctuary in the City

Garrison Cove Studio

Get away at Crystal Lake
When is the best time to visit Raymond?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 250 | € 238 | € 216 | € 216 | € 242 | € 259 | € 302 | € 293 | € 245 | € 234 | € 238 | € 238 |
| 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 |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Raymond?
Four-legged friends are welcome in Raymond. Choose from more than 90 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Raymond?
Yes! Work meets play with ease at over 120 vacation rentals in Raymond featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Raymond vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Raymond, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly cottage rentals in Raymond?
Raymond has more than 50 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in cabin rentals in Raymond?
Experience the best of Raymond with our cabin rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Raymond have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Raymond. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Raymond have wifi?
Absolutely! We offer over 140 house rentals with wifi in Raymond. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Raymond have a bbq area?
Absolutely! We offer over 100 house rentals with a bbq area in Raymond. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Raymond have a gym?
Absolutely! We offer over 10 house rentals with a gym in Raymond. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Raymond?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Raymond

Total vacation rentals
Explore 270 vacation rentals in Raymond

Nightly prices starting at
Raymond vacation rentals start at € 43 per night before taxes and fees

Verified guest reviews
Over 7,970 verified reviews to help you choose

Family-friendly vacation rentals
220 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 90 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
120 properties have a dedicated workspace

Wi-Fi availability
260 of Raymond vacation rentals include wi-fi access

Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Raymond rentals

4.9 Average rating
Raymond stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with a fire pit Raymond
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- Family-friendly rentals Raymond
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- Pet-friendly rentals Raymond
- Rentals with a patio Raymond
- Rentals with a fireplace Raymond
- Cottage rentals Raymond
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- Waterfront rentals Raymond
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Story Land
- Sunday River Resort
- Scarborough Beach
- Popham Beach, Phippsburg
- Popham Beach State Park
- Pemaquid Beach
- Cranmore Mountain Resort
- Willard Beach
- Pemaquid Point Lighthouse
- King Pine Ski Area
- Cape Neddick Beach
- Gooch's Beach
- East End Beach
- Diana's Baths
- Funtown Splashtown USA
- Crescent Beach State Park
- Coastal Maine Botanical Gardens
- Wolfe's Neck Woods State Park
- Pleasant Mountain Ski Area
- Footbridge Beach
- Conway Scenic Railroad




