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

Holiday Homes in Raymond

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Raymond holiday homes

A cozy living room with a dark gray sofa, two pillows with text, a wooden coffee table, and a ceiling fan.

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 €254
includes taxes & fees
18 Oct - 19 Oct
Cozy 2-bedroom house with shared beach access to Sebago Lake
A living room with a sofa, armchairs, a coffee table, and a patterned rug.

2. Newly Remodeled Cottage with AC- Sebago Lake Area

Newly Remodeled Cottage with AC- Sebago Lake Area
Raymond
The price is €464
includes taxes & fees
15 Oct - 16 Oct
Newly Remodeled Cottage with AC- Sebago Lake Area
A multi-story house with a dock and a children's play 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, (17 reviews)
"We loved the houses and esp the hot tub!"
United States
loie H.
The price is €672
includes taxes & fees
19 Oct - 20 Oct
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
Exterior

4. Cozy 2-bedroom Tiny Home with hot tub, A/C, boat ramp access to quiet lake

Cozy 2-bedroom Tiny Home with hot tub, A/C, boat ramp access to quiet lake
Casco
10.0 out of 10, Exceptional, (2 reviews)
"Clean and tidy"
United States
Edward R.
The price is €273
includes taxes & fees
15 Oct - 16 Oct
Cozy 2-bedroom Tiny Home with hot tub, A/C, boat ramp access to quiet lake
A modern kitchen with a bar area, wooden ceiling, and skylights.

5. The Barnhouse with hot tub

The Barnhouse with hot tub
New Gloucester
9.8 out of 10, Exceptional, (10 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 €318
includes taxes & fees
21 Oct - 22 Oct
The Barnhouse with hot tub
A dining area with a long wooden table, six chairs, and a bench. There are large windows with curtains, a plant, and a view into another room.

6. New and Spacious Family Home Close to Sebago Lake

New and Spacious Family Home Close to Sebago Lake
Standish
The price is €854
includes taxes & fees
16 Oct - 17 Oct
New and Spacious Family Home Close to Sebago Lake
A modern living room with a brown leather sofa, a rustic coffee table, and a dining area with a white table and chairs.

7. Windham Lakefront: Fire Pit and Modern Comforts

Windham Lakefront: Fire Pit and Modern Comforts
Windham
9.6 out of 10, Exceptional, (4 reviews)
"It was perfect for our girls trip to Portland. Private, surrounded by woods, cozy and clean! We even saw wild turkeys and deer in the yard."
United States
Jonny D.
The price is €775
includes taxes & fees
28 Oct - 29 Oct
Windham Lakefront: Fire Pit and Modern Comforts
A modern cabin with a large glass facade, a hot tub, and wooden steps leading to the entrance.

8. LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard

LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard
Naples
9.8 out of 10, Exceptional, (9 reviews)
"Fantastic home! We had a great time here and look forward to booking again."
United States
Gina P.
The price is €869
includes taxes & fees
21 Oct - 22 Oct
LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard
A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

9. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
Quiet Spot in lovely Freeport neighborhood
A wooden cabin with a sloped roof, surrounded by snow-covered trees and a clear sky.

10. Manor Suite,cozy newly renovated,downtown & beach

Manor Suite,cozy newly renovated,downtown & beach
Bridgton
9.0 out of 10, Wonderful, (4 reviews)
"The Manor Suite was cozy and charming. It was walking distance from restaurants and shops. I would have loved to stay longer to explore the area.I hope to stay there again if I return to Bridgton next summer."
United States
Jennifer
The price is €141
includes taxes & fees
28 Oct - 29 Oct
Manor Suite,cozy newly renovated,downtown & beach
A beach with footprints, a person standing, and birds on the sand.

11. Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Buxton
7.4 out of 10, Good, (3 reviews)
"The property was unique, with lots of updates to the interior that met and even exceeded our needs (4 TV's!). New appliances and fully stocked with kitchen-ware. Plenty of towels and beds to indeed sleep 10 as described. The host has thought carefully about what you might need during your stay. Outdoor seating is plentiful so if the weather is good, you're all set for hanging out."
United States
Annette
The price is €307
includes taxes & fees
20 Oct - 21 Oct
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
A loft-style bedroom with a sloped ceiling, a ceiling fan, a bed, a desk, and a kitchenette.

12. Peaceful Barn Loft near Sebago Lake and Conway, NH

Peaceful Barn Loft near Sebago Lake and Conway, NH
Hiram
The price is €184
includes taxes & fees
15 Oct - 16 Oct
Peaceful Barn Loft near Sebago Lake and Conway, NH
Dining

13. ANY BIG PARTY!!!!

ANY BIG PARTY!!!!
Standish
8.0 out of 10, Very good, (2 reviews)
"Beautiful property, spacious, plenty of beds and super easy to get to the lake. Owner was very responsive throughout the process."
United States
Logan R.
The price is €1,424
includes taxes & fees
15 Oct - 16 Oct
ANY BIG PARTY!!!!
A window with a view of a snowy landscape and bare trees.

14. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is €297
includes taxes & fees
18 Oct - 19 Oct
Tranquility between the Lakes & Sea
A living room with a sofa, armchair, wooden coffee table, and a potted plant.

15. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
10.0 out of 10, Exceptional, (1 review)
"Great property well kept and close to everything we wanted to do"
United States
boodu
Fully Updated Airy Historic Home in South Freeport
A rustic room with a wooden ceiling, a hot tub, a black leather chair, and a small table with a flag.

16. Ell Suite walk to town beach

Ell Suite walk to town beach
Bridgton
8.8 out of 10, Excellent, (3 reviews)
"Great spot as advertised "
United States
mark l.
The price is €141
includes taxes & fees
28 Oct - 29 Oct
Ell Suite walk to town beach
A dirt path in a park with autumn foliage.

17. 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 €562
includes taxes & fees
15 Oct - 16 Oct
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

18. Luxe 5 Bed/ 3 Bath with Game Room & AC

Luxe 5 Bed/ 3 Bath with Game Room & AC
Yarmouth
10.0 out of 10, Exceptional, (4 reviews)
"What a great place to stay! The home is very clean and very quiet. Our host was very responsive to any questions we had. We would book this one over and over again."
United States
Michelle T.
Luxe 5 Bed/ 3 Bath with Game Room & AC
A view through a window of a lake surrounded by trees and a small house.

19. Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway

Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway
Bridgton
10.0 out of 10, Exceptional, (65 reviews)
"This was our second stay at Windsor Cottage, and it was just as wonderful as the first! The cottage is always spotless, beautifully furnished, and truly feels like a home away from home. We love the lake access, the pet-friendly accommodations, and being just minutes from downtown Bridgton. We can’t wait to come back again!"
United States
Cortney C.
The price is €362
includes taxes & fees
19 Oct - 20 Oct
Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway
A modern living room with a teal sofa, two glasses of white wine, a tray of food, and a decorative candle on a wooden table.

20. Sleeps 16+ | W/D | Parking | 15 mins to Old Port

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
10.0 out of 10, Exceptional, (1 review)
"This place was excellent, very clean, and the check-in/checkout process was very easy. The unit is broken into 3 distinct apartments with the upstairs being a one bedroom suite. However, all of the units are accessible to each other through stairs so it's convenient for staying connected while also having some separate space."
United States
damean s.
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
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

Inn at St John Portland In-Town

Inn at St John Portland In-Town

8/10 Good
"Breakfast was very good. Free parking. But no elevator -- and steep stairs."
Peter 1-night trip
Posted 2 hours ago
Inn at St John Portland In-Town

Find out more about Raymond

Raymond Holiday Homes information

Number of reviews
103
Accommodation
798 Holiday Homes
Lowest Price
€141
Highest Price
€1,424