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

LUX Designer Private Waterfront Hot Tub - Secluded
Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

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.

Lovely Lakefront Cottage - Book Your Fall GetAway!
Whether you’re craving a peaceful retreat or a winter adventure, this lakefront cottage has everything you need to create unforgettable memories. Cozy up by the fire, snowshoe the lake, or simply soak in the serene beauty of the season. Embrace the charm of winter on the lake, the perfect getaway for families, couples, or solo adventurers. Don't wait for summer to fall in love with this hidden gem. NOTE: Winter & Spring guests should be comfortable navigating winter weather/seasonal conditions.

Rustic knotty pine getaway
lovely completely newly remodeled 2 bedroom 1-1/2 bath completely private upstairs unit with kitchen and private screened in deck. It has a private entrance with plenty of off street parking. located in Maine's lake region area. Walking distance to Raymond beach on Sebago lake. 5 miles to restaurants, shopping and local entertainment. 15 Miles from Portland. 30 to 60 minutes to winter skiing. Kayak, boat, and jet ski rentals nearby. 30 minutes to casino. Electric Vehicle charging on site.

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.

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!

The Great Escape - Picturesque Sebago Lake
Experience an intimate home with stunning Sebago Lake views. This inviting retreat features 4 bedrooms and 8 beds, ensuring a restful stay for up to 12 guests. The enormous kitchen island is perfect for gathering, whether preparing a family feast or enjoying casual conversations. Snuggle up by the propane fireplace in the living area, or spend evenings around the outdoor firepit, making s’mores under the stars. The breathtaking lake views create a serene backdrop for your vacation.

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!

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

Gorgeous 1BR apartment, walk to Sebago Lake
Centrally located in the Sebago Lake region, this spacious 1BR apartment is the perfect home base for your Southern Maine adventures! Just a 30 minute drive to Portland, this location also provides great access to skiing, swimming, hiking, snow-tubing, coastal exploring, outlet shops in Freeport and North Conway, and the White Mountains of New Hampshire. A full modern kitchen and bath, with an additional fold-out sofa in the living room. Second floor above a daytime business.

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.

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
Popular amenities for Raymond holiday rentals
Stay near Raymond's top sights
Other great holiday rentals in Raymond

Idyllic Lakeside Cabin Winter Getaway

Cozy Waterfront Maine Retreat

Charming & Cozy Lakefront Home - Private Beach!

Maine Vacation Home on the Water

Trickey Moose Family Retreat | Near Skiing Jacuzzi

Sebago Lake Retreat | Views, Fire Pit, Family Fun

Sebago Lake Beach Paradise

Dockside Dreams
When is the best time to visit Raymond?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $371 SGD | $353 SGD | $321 SGD | $321 SGD | $359 SGD | $385 SGD | $448 SGD | $435 SGD | $363 SGD | $346 SGD | $353 SGD | $353 SGD |
| 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 holiday rentals in Raymond

Total holiday rentals
Explore 270 holiday rentals in Raymond

Nightly prices starting at
Raymond holiday rentals start at $64 SGD per night before taxes and fees

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

Family-friendly holiday rentals
220 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 90 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
120 properties have a dedicated workspace

Wifi availability
260 of Raymond holiday rentals include wifi 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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- 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
- King Pine Ski Area
- Cape Neddick Beach
- Pemaquid Point Lighthouse
- Gooch's Beach
- East End Beach
- Diana's Baths
- Funtown Splashtown USA
- Crescent Beach State Park
- Coastal Maine Botanical Gardens
- Footbridge Beach
- Pleasant Mountain Ski Area
- Wolfe's Neck Woods State Park
- Palace Playland




