
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.

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.

Kayak to the Causeway-50s cottage with modern vibe
Find out why the Maine life is the best life at Moonstone Cottage. Play on the shores of Long Lake, stroll the Naples Causeway, eat your way around Portland, and hike the mountains of western Maine before coming home to relax around the fire pit, lounge on the deck, and get a feel for the way life should be. Kayaks are waiting for you on the private association beach, or rent a boat from the marina to explore 40 miles of open water. Restaurants, live music, and the market are a short walk away.

Amazing Views! Perfect Location. Loft style feel.
Oh the VIEW! City views and a beautiful park like old cemetery. Cozy, sunny private apartment in a quiet, Owner Occupied building. Perfect East End location for exploring all of Portland Just 2 blocks from Duckfat, Eventide and many restaurants, breweries and distilleries Comfy living room with a 55" TV and seating to take in the view. Fully equipped eat in kitchen, tile shower and a wonderful King size bed to watch the sun rise Includes Reserved Off street parking. License #STHR-000980

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.

Stunning Library Tiny Home *Private Hot Tub*King B
Welcome to The Tiny Library - Maine's most unique tiny home! This antique library building has been newly renovated into a cozy getaway for bibliophiles and library lovers alike. Its book-lined shelves and dark academia decor, along with modern amenities and high quality bedding ensure a memorable stay, while the gas fireplace and hot tub provide the perfect ambiance for rest and relaxation. Whether you're a bookworm or just in need of a quiet escape, The Tiny Library is the perfect retreat.

Lobstermen's ocean-front cottage
Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

Dreamy Post&Beam Hideaway Near Portland & Freeport
Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

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!

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.

1BR cozy, luxurious getaway @ Krista's Guesthouse
Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

The Barnhouse with hot tub
Get away with your whole family at this peaceful home in the country. Hear the frogs chirping in the pond, birds tweeting in the treetops and watch chickens roam around. Enjoy the clear, starry nights while relaxing in the hot tub or cozying up by the fire. Centrally located between coast and mountains. Head a hour north to take the family hiking or on the slopes to enjoy the mountains. Head 40 minutes south to take in the coast and see the iconic Maine lighthouse.

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 vacation rentals
Stay near Raymond's top sights
Raymond house rentals

Lakefront Getaway

Cottage with private beach access to sebago lake

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit

Dreamy Mountain Views w/ Hot Tub + Wood Stove

Beautiful Coastal Maine Getaway

Unplug at a Beachy Bolthole with Classic New England Style

Beautiful Home In Gorham Maine

In Village, SPA, Best location, Fire Place, 1 bed
Lakefront house rentals in Raymond

The Lazy Hummingbird: Little Sebago Home w/ Sauna

Beautiful lake-side home close to Portland Maine

Tranquil Pondside Retreat

Scandinavian Lakehouse - King Bed - Pet friendly

Beautiful Lakefront View, on Sebago Lake

Private Lake House, Firepit & Amazing Sunset Views

Lakefront haven near Shawnee-25mi to North Conway

Water's Edge- A family-friendly beachfront stay
Other great vacation rentals in Raymond

Songo Lock Cabins #2 (Located at Historic Site)

The Bunkhouse at Sebago Lake

The Maine Frame | Modern A-Frame Cabin in Freeport

Springer Park! adorable guesthouse very stylish!.

Cozy Tiny Home | Fireplace • 9 Miles to Portland

Sunny 2-BR 5 min to Bates & River Trails

Wren Cabin + Wood fired Sauna

Solar Suite surrounded by Nature
When is the best time to visit Raymond?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,061 | ﺩ.ﺇ1,010 | ﺩ.ﺇ918 | ﺩ.ﺇ918 | ﺩ.ﺇ1,028 | ﺩ.ﺇ1,102 | ﺩ.ﺇ1,282 | ﺩ.ﺇ1,245 | ﺩ.ﺇ1,039 | ﺩ.ﺇ992 | ﺩ.ﺇ1,010 | ﺩ.ﺇ1,010 |
| 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 vacation rentals in Raymond?
Raymond has more than 220 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in cottage rentals in Raymond?
Experience the best of Raymond with our cottage rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Raymond have air conditioning?
Absolutely! We offer over 30 cottage 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 cottage rentals in Raymond have a bbq area?
Absolutely! We offer over 40 cottage 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 Cottage Rentals in Raymond?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 40 homes with a bbq area, over 30 homes with air conditioning, over 50 homes with wifi, 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 ﺩ.ﺇ184 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 patio 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
- King Pine Ski Area
- Willard Beach
- East End Beach
- Cape Neddick Beach
- Gooch's Beach
- Pemaquid Point Lighthouse
- Diana's Baths
- Funtown Splashtown USA
- Coastal Maine Botanical Gardens
- Crescent Beach State Park
- Wolfe's Neck Woods State Park
- Footbridge Beach
- Palace Playland
- Pleasant Mountain Ski Area




