A flowing river with large rocks, surrounded by trees and a snowy bank.

Raymond Vacation Rentals

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Our top choices for Raymond vacation rentals

1. Cozy 2-bedroom house with shared beach access to Sebago Lake

Cozy 2-bedroom house with shared beach access to Sebago Lake
Raymond
The price is CA $315
CA $392 total
includes taxes & fees
Aug 26 - Aug 27
Cozy 2-bedroom house with shared beach access to Sebago Lake

2. Newly Remodeled Cottage with AC- Sebago Lake Area

Newly Remodeled Cottage with AC- Sebago Lake Area
Raymond
The price is CA $415
CA $721 total
includes taxes & fees
Aug 31 - Sep 1
Newly Remodeled Cottage with AC- Sebago Lake Area

3. Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats

Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
Casco
9.8 out of 10, Exceptional, (15 reviews)
"Our stay at this vacation home was wonderful! We had the best time relaxing and enjoying the fall weather. The property manager was responsive and helpful upon check in and check out. We will most definitely be staying there again!"
United States
Michie K.
The price is CA $587
CA $1,381 total
includes taxes & fees
Aug 31 - Sep 1
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats

4. Lakefront cabin on Brandy Pond with dock, deck, firepit, kayaks & paddleboard

Lakefront cabin on Brandy Pond with dock, deck, firepit, kayaks & paddleboard
Naples
9.2 out of 10, Wonderful, (55 reviews)
"Amazing location! Cabin was perfect! Had such a wonderful time. "
United States
Jillene F.
The price is CA $441
CA $1,073 total
includes taxes & fees
Aug 30 - Aug 31
Lakefront cabin on Brandy Pond with dock, deck, firepit, kayaks & paddleboard

5. THE LILLIPAD.Off-grid A frame. Sebago lake region!

THE LILLIPAD.Off-grid A frame. Sebago lake region!
Standish
9.8 out of 10, Exceptional, (14 reviews)
"Had a wonderful overnight - was perfect weekend getaway. Was great being in nature!"
United States
Alex D.
The price is CA $328
CA $405 total
includes taxes & fees
Aug 16 - Aug 17
THE LILLIPAD.Off-grid A frame. Sebago lake region!

6. The Barnhouse with hot tub

The Barnhouse with hot tub
New Gloucester
9.8 out of 10, Exceptional, (9 reviews)
"This was the perfect spot for my friends and I who were attending a wedding down the road! Great location, lovely property and very clear instructions from the hosts! "
United States
Jen V.
The price is CA $265
CA $502 total
includes taxes & fees
Aug 25 - Aug 26
The Barnhouse with hot tub

7. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
9.6 out of 10, Exceptional, (43 reviews)
"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"
United States
Genevieve W.
The price is CA $566
CA $811 total
includes taxes & fees
Aug 16 - Aug 17
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

8. Modern cabin w/ full bath & kitchenette - 03

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (7 reviews)
"Easy check in process. More than clean, it looked brand new. Overall a great stay. Kitchen was well stocked with plates, utensils, and cookware. "
United States
Michael H.
The price is CA $481
CA $716 total
includes taxes & fees
Sep 6 - Sep 7
Modern cabin w/ full bath & kitchenette - 03

9. Cozy Library Tiny Home *Private Hot Tub* King Bed *Minutes to Lakes & Hiking

Cozy Library Tiny Home *Private Hot Tub* King Bed *Minutes to Lakes & Hiking
Bridgton
10.0 out of 10, Exceptional, (15 reviews)
"Very quaint and quiet, we enjoyed our staying very much would heavily recommend"
United States
Jacob B.
The price is CA $315
CA $585 total
includes taxes & fees
Aug 18 - Aug 19
Cozy Library Tiny Home *Private Hot Tub* King Bed *Minutes to Lakes & Hiking

10. Modern dome w/ full bath + spa access - 04

Modern dome w/ full bath + spa access - 04
Freeport
10.0 out of 10, Exceptional, (4 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
The price is CA $657
CA $964 total
includes taxes & fees
Sep 1 - Sep 2
Modern dome w/ full bath + spa access - 04

11. Cozy 3BR | Pet Friendly | Near Portland | Parking

Cozy 3BR | Pet Friendly | Near Portland | Parking
Westbrook
10.0 out of 10, Exceptional, (13 reviews)
"We had a great stay here. It was very clean and conveniently located."
United States
Angela B.
The price is CA $280
CA $686 total
includes taxes & fees
Aug 9 - Aug 10
Cozy 3BR | Pet Friendly | Near Portland | Parking

12. Barn on Pleasant-walk to Highland beach & town

Barn on Pleasant-walk to Highland beach & town
Bridgton
10.0 out of 10, Exceptional, (26 reviews)
"Absolutely beautiful place to stay! The room was very welcoming and cozy. "
United States
Robyn N.
The price is CA $221
CA $271 total
includes taxes & fees
Aug 16 - Aug 17
Barn on Pleasant-walk to Highland beach & town

13. City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (131 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
City Amenities, Casco Bay Sunrises and Natural Beauty

14. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (108 reviews)
"Really nice room and location"
United States
Victoria
The price is CA $445
CA $590 total
includes taxes & fees
Sep 1 - Sep 2
The Weldon Hotel

15. Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is CA $479
CA $522 total
includes taxes & fees
Aug 23 - Aug 24
Fortland Island Campground

16. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very good, (13 reviews)
"A perfectly decent place to stay, plenty of restaurants and bars within reasonable walking distance. Neighborhood is a bit rough, as the listing mentioned, but no problems while I was there. Response time on questions to the host could be better."
Canada
Brian
The price is CA $147
CA $249 total
includes taxes & fees
Aug 11 - Aug 12
Studio Apartment near downtown Walkable!

17. Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (23 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is CA $276
CA $443 total
includes taxes & fees
Aug 31 - Sep 1
Charming Studio apartment with WiFi, AC in welcoming Portland

18. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (139 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is CA $276
CA $435 total
includes taxes & fees
Sep 6 - Sep 7
Adorable Portland getaway on the Eastern Promenade

19. Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is CA $331
CA $534 total
includes taxes & fees
Aug 9 - Aug 10
Peaceful & minutes from the Old Port with private parking

20. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
9.8 out of 10, Exceptional, (108 reviews)
"Lovely view and accessibility to the Old Port area. Enjoyed our relaxing stay! Thanks Dan! "
United States
David E.
The price is CA $420
CA $649 total
includes taxes & fees
Aug 23 - Aug 24
Ocean View East End Studio in a Historic Victorian
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Raymond Hotel Reviews

Find out more about Raymond

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Raymond. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Raymond?

Yes, you can find vacation rentals close to popular points of interest in Raymond, or you can go with a more secluded option if you're looking for relaxation.

What's the top vacation rental that Raymond has to offer?

Breathtaking Lake Views: Visitors give good reviews to this Raymond vacation home rental, which is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Raymond?

With 89 Expedia vacation rentals, you're sure to find just the right place for your Raymond stay.

What’s there to see and do in Raymond?

Little Sebago Lake and Crescent Lake are a couple of lovely local spots to get outside and enjoy nature. While here, Sebago Lake and Rattlesnake Mountain Trail are other places worth a visit.

What’s a vacation rental in Raymond like?

Vacation rentals are privately owned properties you can book for short or long periods in Raymond. Vacation rentals offer amenities like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family getaway.